N-(isoxazol-3-yl)-aryl-carboxylic acid amides and use thereof as herbicides

ABSTRACT

The invention relates to N-(isoxazol-3-yl)-aryl-carboxylic acid amides and use thereof as herbicides. In formula (I), A stands for N or C—Y. R, V, X, Y, and Z stand for groups such as hydrogen, halogen, and organic groups such as substituted alkyl.

The invention relates to the technical field of the herbicides,especially that of the herbicides for selective control of broad-leavedweeds and weed grasses in crops of useful plants.

WO 2011/035874 A1 discloses N-(1,2,5-oxadiazol-3-yl)benzamides and usethereof as herbicides. WO 2012/028579 A1 discloses N-(tetrazol-5-yl)-and N-(triazol-5-yl)arylcarboxamides and their use as herbicides.Perfluoroalkylisoxazole derivatives and their use as herbicides areknown from JP 01009978 A.

Under the following CAS numbers, the compounds which are mentionedfollowing each one are known:

-   1283281-40-2: 4,5-difluoro-2-nitro-N-(1,2-oxazol-3-yl)benzamide,-   1275071-21-0: 2-bromo-4-fluoro-N-(1,2-oxazol-3-yl)benzamide,-   950245-82-6: 2,4-dichloro-N-(1,2-oxazol-3-yl)benzamide,-   932855-85-1: 2,4-dimethoxy-N-(1,2-oxazol-3-yl)benzamide,-   886633-07-4: 2,4-diethoxy-N-(1,2-oxazol-3-yl)benzamide,-   886630-79-1: 2-chloro-4-fluoro-N-(1,2-oxazol-3-yl)benzamide,-   830341-63-4: 2-chloro-4,5-difluoro-N-(1,2-oxazol-3-yl)benzamide,-   587852-24-2: 2,4,5-trimethoxy-N-(1,2-oxazol-3-yl)benzamide, and-   1408387-94-9: 4-bromo-4-fluoro-N-(1,2-oxazol-3-yl)benzamide.

No herbicidal effect of the compounds known by their CAS numbers hasbeen disclosed. US20090163545 A1 describes a pharmacological activity ofthe compound 2-methoxy-4-(methylsulfanyl)-N-(1,2-oxazol-3-yl)benzamide.

However, the compounds known from these documents exhibit zero orfrequently inadequate herbicidal efficacy. It is an object of thepresent invention to provide further herbicidally active compounds.

It has now been found that N-(isoxazol-3-yl)-arylcarboxamides whichcarry hydrogen in the 5-position of the isoxazole ring and certainsubstituents in the 4-position of the isoxazole ring and in thearylcarboxylic acid moiety are particularly suitable for use asherbicides.

Accordingly, the present invention providesN-(isoxazol-3-yl)arylcarboxamides of the formula (I) or salts thereof

in whichA represents N or CY,R represents hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl,halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,(C₂-C₆)-alkenyl, (C₂-C₆)-alkenyloxy, (C₂-C₆)-haloalkenyl,(C₂-C₆)-alkynyl, (C₂-C₆)-alkynyloxy, (C₂-C₆)-haloalkynyl,cyano-(C₁-C₆)-alkyl, cyano, nitro, methylsulfenyl, methylsulfinyl,methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl,ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl,methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen,amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl,methoxymethyl, or heteroaryl, heterocyclyl or phenyl, each of which issubstituted by s radicals from the group consisting of methyl, ethyl,methoxy, trifluoromethyl and halogen,X represents nitro, halogen, cyano, formyl, thiocyanato, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, COR¹, COOR¹, OCOOR¹, NR¹COOR¹,C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂, C(O)NR¹OR¹, OR², OCOR¹, OSO₂R²,S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹,(C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹,(C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-SO₂OR¹, (C_(r)C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹,(C₁-C₆)-alkyl-NR¹SO₂R², NR₁R₂, P(O)(O R⁵)₂, CH₂P(O)(OR⁵)₂,(C₁-C₆)-alkyl-heteroaryl, (C₁-C₆)-alkyl-heterocyclyl, where the twolast-mentioned radicals are each substituted by s radicals from thegroup consisting of halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy and halo-(C₁-C₆)-alkoxy, andwhere heterocyclyl carries n oxo groups,Y represents hydrogen, nitro, halogen, cyano, thiocyanato,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, COOR¹, OCOOR¹, NR¹COOR¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂,CO(NOR¹)R¹, CHNOR¹, CH₂ONCR³)₂, NR¹SO₂R², NR¹COR¹, OR¹, OSO₂R²,S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂ (C₁-C₆)-alkyl-S(O)_(n)R², NS(O)R⁸R⁷,S(O)R⁸NR⁹, (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R²,(C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-CN, (C₁-C₆)-alkyl-SO₂OR¹,(C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹,(C₁-C₆)-alkyl-NR¹SO₂R², N(R¹)₂, P(O)(OR⁵)₂, CH₂P(O)(OR⁵)₂,(C₁-C₆)-alkylphenyl, (C₁-C₆)-alkylheteroaryl, (C₁-C₆)-alkylheterocyclyl,phenyl, heteroaryl or heterocyclyl, where the 6 last-mentioned radicalsare each substituted by s radicals from the group consisting of halogen,nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, and where heterocyclylcarries 0 to 2 oxo groups,Z represents halogen, cyano, thiocyanato, nitro, (C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, COOR¹, OCOOR¹, NR¹COOR¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂,C(O)NR¹OR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹,(C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹,(C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-SO₂R¹, (C₁-C₆)-alkyl-SO₂OR¹,(C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹,(C₁-C₆)-alkyl-NR¹SO₂R², NR¹R², P(O)(OR⁵)₂, heteroaryl, heterocyclyl orphenyl, where the three last-mentioned radicals are each substituted bys radicals from the group consisting of halogen, nitro, cyano,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy or halo-(C₁-C₆)-alkoxy, and whereheterocyclyl carries 0 to 2 oxo groups, orZ may also represent hydrogen if Y represents the S(O)_(n)R² radical,V represents hydrogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, S(O)_(n)—(C₁-C₆)-alkyl,S(O)_(n)—(C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, halogen, nitroor cyano,R¹ represents hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl,(C₂-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl,(C₃-C₆)-halocycloalkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl,heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 last-mentioned radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR⁴,NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries 0to 2 oxo groups,R² represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 last-mentioned radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOW,NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries 0to 2 oxo groups,R³ represents hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,R⁴ represents (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl or phenyl,R⁵ represents methyl or ethyl,R⁶ and R⁷ independently of one another each represent (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,halo-(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, phenyl, heteroaryl or heterocyclyl,where the three last-mentioned radicals are each substituted by sradicals from the group consisting of nitro, halogen, cyano,thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S andR¹O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxo groups,orR⁶ and R⁷ together with the sulfur atom to which they are attached forma 3- to 8-membered unsaturated, partly saturated or saturated ring whichcontains, apart from the carbon atoms and apart from the sulfur atom ofthe sulfoximino group, in each case m ring members from the groupconsisting of N(R¹), O and S(O)_(n), and where this ring is in each casesubstituted by s radicals from the group consisting of nitro, halogen,cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R²(O)_(n)S,R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl, and where this ring carriesn oxo groups,R⁸ represents (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, each ofwhich is substituted by s radicals from the group consisting of nitro,halogen, cyano, thiocyanato, (C₃-C₆)-cycloalkyl, R¹(O)C, R¹(R¹ON═)C,R¹O(O)C, (R¹)₂N(O)C, R¹(R¹O)N(O)C, R²(O)₂S(R¹)N(O)C, R¹O(O)₂S(R¹)N(O)C,(R¹)₂N(O)₂S(R¹)N(O)C, R¹S(O)C, R¹O, R¹(O)CO, R²(O)₂SO, R²O(O)CO,(R¹)₂N(O)CO, (R¹)₂N, R¹O(R¹)N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N,(R¹)₂N(O)C(R¹)N, R¹O(O)₂S(R¹)N, (R¹)₂N(O)₂S(R¹)N, R²(O)_(n)S, R¹C(O)S,R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S, R²O(O)C(R¹)N(O)₂S,(R¹)₂N(O)C(R¹)N(O)₂S and (R⁵O)₂(O)P,or(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, phenyl, phenyl-(C₁-C₆)-alkyl,heteroaryl, heteroaryl-(C₁-C₆)-alkyl, heterocyclyl,heterocyclyl-(C₁-C₆)-alkyl, phenyl-O—(C₁-C₆)-alkyl,heteroaryl-O—(C₁-C₆)-alkyl, heterocyclyl-O—(C₁-C₆)-alkyl,phenyl-N(R¹)—(C₁-C₆)-alkyl, heteroaryl-N(R¹)—(C₁-C₆)-alkyl,heterocyclyl-N(R¹)—(C₁-C₆)-alkyl, phenyl-S(O)_(n)—(C₁-C₆)-alkyl,heteroaryl-S(O)_(n)—(C₁-C₆)-alkyl orheterocyclyl-S(O)_(n)—(C₁-C₆)-alkyl, each of which is substituted in thecyclic moiety by s radicals from the group consisting of nitro, halogen,cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N(O)C,R¹(R¹O)N(O)C, R²(O)₂S(R¹)N(O)C, R¹O(O)₂S(R¹)N(O)C, (R¹)₂N(O)₂S(R¹)N(O)C,R¹S(O)C, R¹O, R¹(O)CO, R²(O)₂SO, R²O(O)CO, (R¹)₂N(O)CO, (R¹)₂N,R¹O(R¹)N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N,R¹O(O)₂S(R¹)N, (R¹)₂N(O)₂S(R¹)N, R²(O)_(n)S, R¹C(O)S, R¹O(O)₂S,(R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S, R²O(O)C(R¹)N(O)₂S, (R¹)₂N(O)C(R¹)N(O)₂S,(R⁵O)₂(O)P and R¹O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxogroups,R⁹ represents hydrogen, nitro, halogen, cyano, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₃-C₆)-alkenyl, halo-(C₃-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, R¹(O)C, R²O(O)C, (R¹)₂N(O)C,R²S(O)C, (R¹)₂N(S)C, R¹(R¹O)N(O)C, R²(O)₂S(R¹)N(O)C,(R¹)₂N(O)₂S(R¹)N(O)C, R¹O, (R¹)₂N, R²(O)_(n)S,(R²)₃Si—(C₁-C₆)-alkyl-(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S,R²O(O)C(R¹)N(O)₂S, (R¹)₂N(O)C(R¹)N(O)₂S, R²(O)₂S(R¹)N(O)₂S, (R⁵O)₂(O)P,(R²)₃Si, R¹(O)C—(C₁-C₆)-alkyl, R¹O(O)C—(C₁-C₆)-alkyl,(R¹)₂N(O)C—(C₁-C₆)-alkyl, (R¹O)(R¹)N(O)C—(C₁-C₆)-alkyl,R²(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, R¹O(O)₂S(R₁)N(O)C—(C₁-C₆)-alkyl,(R¹)₂N(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl,R¹(O)CO—(C₁-C₆)-alkyl, R²(O)₂SO—(C₁-C₆)-alkyl, R²O(O)CO—(C₁-C₆)-alkyl,(R¹)₂N(O)CO—(C₁-C₆)-alkyl, (R¹)₂N—(C₁-C₆)-alkyl,R¹(O)C(R¹)N—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N—(C₁-C₆)-alkyl,R²O(O)C(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N—(C₁-C₆)-alkyl,R¹O(O)₂S(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S(R¹)N—(C₁-C₆)-alkyl,R²(O)_(n)S—(C₁-C₆)-alkyl, R¹O(O)₂S—(C₁-C₆)-alkyl,(R¹)₂N(O)₂S—(C₁-C₆)-alkyl, R¹(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl,R²O(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl,(R⁵O)₂(O)P—(C₁-C₆)-alkyl, (R²)₃Si—(C₁-C₆)-alkyl,orphenyl, heteroaryl, heterocyclyl, phenyl-(C₁-C₆)-alkyl,heteroaryl-(C₁-C₆)-alkyl or heterocyclyl-(C₁-C₆)-alkyl, each of which issubstituted in the cyclic moiety by s radicals from the group consistingof nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, R¹O(O)C, (R¹)₂N(O)C, R¹O,(R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl, andwhere heterocyclyl carries n oxo groups,m represents 0, 1, 2, 3 or 4,n represents 0, 1 or 2,s represents 0, 1, 2 or 3,except for compounds in which R and Y each represent hydrogen and at thesame timea) Z represents fluorine and X represents nitro, bromine or chlorine, orb) Z represents chlorine and X represents chlorine, orc) Z represents methoxy and X represents methoxy, ord) Z represents ethoxy and X represents ethoxy, ore) Z represents methyl sulfide and X represents methoxy.

In the formula (I) and all the formulae which follow, alkyl radicalshaving more than two carbon atoms may be straight-chain or branched.Alkyl radicals are, for example, methyl, ethyl, n- or i-propyl, n-, i-,t- or 2-butyl, pentyls, hexyls such as n-hexyl, i-hexyl and1,3-dimethylbutyl. Halogen is fluorine, chlorine, bromine or iodine.

Heterocyclyl is a saturated, partly saturated or fully unsaturatedcyclic radical which contains 3 to 6 ring atoms, of which 1 to 4 arefrom the group of oxygen, nitrogen and sulfur, and which mayadditionally be fused by a benzo ring. For example, heterocyclyl ispiperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl andoxetanyl.

Heteroaryl represents an aromatic cyclic radical which contains 3 to 6ring atoms, of which 1 to 4 are from the group of oxygen, nitrogen andsulfur, and which may additionally be fused by a benzo ring. Forexample, heteroaryl is benzimidazol-2-yl, furanyl, imidazolyl,isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl,pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl,1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl,1,3,4-oxadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,5-triazolyl,1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl,2H-1,2,3,4-tetrazolyl, 1H-1,2,3,4-tetrazolyl, 1,2,3,4-oxatriazolyl,1,2,3,5-oxatriazolyl, 1,2,3,4-thiatriazolyland 1,2,3,5-thiatriazolyl.

If a group is polysubstituted by radicals, this is understood to meanthat this group is substituted by one or more identical or differentradicals from those mentioned.

Depending on the nature of the substituents and the manner in which theyare attached, the compounds of the general formula (I) may be present asstereoisomers. If, for example, one or more asymmetric carbon atoms arepresent, enantiomers and diastereomers may occur. Stereoisomers likewiseoccur when n is 1 (sulfoxides). Stereoisomers can be obtained from themixtures obtained in the preparation by customary separation methods,for example by chromatographic separation processes. It is likewisepossible to selectively prepare stereoisomers by using stereoselectivereactions with use of optically active starting materials and/orauxiliaries. The invention also relates to all the stereoisomers andmixtures thereof that are encompassed by the general formula (I) but arenot defined specifically.

Preference is given to compounds of the general formula (I) in which

A represents N or CY,X represents nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,halo-(C₃-C₆)-cycloalkyl, C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, OR², OCOR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R²,NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹,(C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂,(C₁-C₆)-alkyl-NR¹COR¹ or (C₁-C₆)-alkyl-NR¹SO₂R²,(C₁-C₆)-alkylheteroaryl, (C₁-C₆)-alkylheterocyclyl, where the twolast-mentioned radicals each by s radicals from the group consisting ofhalogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, S(O)_(n)—(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy and halo-(C₁-C₆)-alkoxy, and where heterocyclyl carries 0to 2 oxo groups,Y represents hydrogen, nitro, halogen, cyano, thiocyanato,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, OR¹, COOR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, N(R¹)₂,NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹,(C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂,(C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², (C₁-C₆)-alkylphenyl,(C₁-C₆)-alkyl-heteroaryl, (C₁-C₆)-alkyl-heterocyclyl, phenyl, heteroarylor heterocyclyl, where the 6 last-mentioned radicals are eachsubstituted by s radicals from the group consisting of halogen, nitro,cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, and where heterocyclylcarries 0 to 2 oxo groups,Z represents halogen, cyano, thiocyanato, nitro, (C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, COOR¹, C(O)N(R¹)₂, C(O)NR¹OR¹, OSO₂R², S(O)_(n)R², SO₂OR¹,SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R²,(C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R²,(C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²,1,2,4-triazol-1-yl, orZ may also represent hydrogen if Y represents the S(O)_(n)R² radical,V represents hydrogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, S(O)_(n)—(C₁-C₆)-alkyl,S(O)_(n)—(C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, halogen, nitroor cyano,R represents hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl,halo-(C₁-C₆)-alkyl, (C_(r) C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,cyano-(C₁-C₆)-alkyl, cyano, methylsulfenyl, methylsulfinyl,methylsulfonyl, acetylamino, methoxymethyl, or heteroaryl, heterocyclylor phenyl, each of which is substituted by s radicals from the groupconsisting of methyl, ethyl, methoxy, trifluoromethyl and halogen,R¹ represents hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl,(C₁-C₆)-alkylheteroaryl, heterocyclyl, (C₁-C₆)-alkylheterocyclyl,(C₁-C₆)-alkyl-O-heteroaryl, (C₁-C₆)-alkyl-O-heterocyclyl,(C₁-C₆)-alkyl-NR³-heteroaryl or (C₁-C₆)-alkyl-NR³-heterocyclyl, wherethe 16 last-mentioned radicals are substituted by s radicals from thegroup consisting of cyano, halogen, nitro, OR³, S(O)_(n)R⁴, N(R³)₂,NR³OR³, COR³, OCOR³, NR³COR³, NR³SO₂R⁴, CO₂R³, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries 0to 2 oxo groups,R² represents (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl,(C₁-C₆)-alkylheteroaryl, heterocyclyl, (C₁-C₆)-alkylheterocyclyl,(C₁-C₆)-alkyl-O-heteroaryl, (C₁-C₆)-alkyl-O-heterocyclyl,(C₁-C₆)-alkyl-NR³-heteroaryl or (C₁-C₆)-alkyl-NR³-heterocyclyl, wherethese radicals are substituted by s radicals from the group consistingof cyano, halogen, nitro, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, NR³SO₂R⁴,COR³, OCOR³, NR³COR³, CO₂R³, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries 0to 2 oxo groups,R³ represents hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,R⁴ represents (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl,R⁶ and R⁷ independently of one another each represent (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, phenyl,heteroaryl or heterocyclyl, where the three last-mentioned radicals areeach substituted by s radicals from the group consisting of nitro,halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, R¹O(O)C, (R¹)₂N(O)C, R¹O,(R¹)₂N, R²(O)_(n)S and R¹O—(C₁-C₆)-alkyl, and where heterocyclyl carriesn oxo groups,or R⁶ and R⁷ together with the sulfur atom to which they are attachedform a 3- to 8-membered unsaturated, partly saturated or saturated ringwhich contains, in addition to the carbon atoms and in addition to thesulfur atom of the sulfoximino group, in each case m ring members fromthe group consisting of N(R¹), 0 and S(O)_(n), and where this ring is ineach case substituted by s radicals from the group consisting ofhalogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, R¹O(O)C, (R¹)₂N(O)C, R¹O,(R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl, andwhere this ring carries n oxo groups,R⁸ represents (C₁-C₆)-alkyl which is in each case substituted by sradicals from the group consisting of halogen, cyano,(C₃-C₆)-cycloalkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N(O)C,R²(O)₂S(R¹)N(O)C, R¹O, (R¹)₂N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N,(R¹)₂N(O)C(R¹)N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S,R²O(O)C(R¹)N(O)₂S and (R¹)₂N(O)C(R¹)N(O)₂S or(C₃-C₆)-cycloalkyl which is in each case substituted by s radicals fromthe group consisting of halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, R¹O(O)C and (R¹)₂N(O)C,R⁹ represents hydrogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,R¹(O)C, R²O(O)C, (R¹)₂N(O)C, R²(O)₂S, R¹(O)C—(C₁-C₆)-alkyl,R¹O(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)C—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl,(R¹)₂N—(C₁-C₆)-alkyl or R²(O)_(n)S—(C₁-C₆)-alkyl,m represents 0, 1 or 2,n represents 0, 1 or 2,s represents 0, 1, 2 or 3,except for compounds in which R and Y each represent hydrogen and at thesame timea) Z represents fluorine and X represents nitro, bromine or chlorine, orb) Z represents chlorine and X represents chlorine, orc) Z represents methoxy and X represents methoxy, ord) Z represents ethoxy and X represents ethoxy, ore) Z represents methyl sulfide and X represents methoxy.

Particular preference is given to compounds of the general formula (I)in which

A represents N or CY,X represents nitro, halogen, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, OR², S(O)_(n)R², (C₁-C₆)-alkyl-S(O)_(n)R²,(C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂,(C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², (C₁-C₆)-alkylheteroaryl,(C₁-C₆)-alkylheterocyclyl, where the two last-mentioned radicals areeach substituted by s radicals from the group consisting of halogen,(C_(r) C₆)-alkyl, halo-(C₁-C₆)-alkyl, S(O)_(n)—(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, and where heterocyclyl carries 0 to2 oxo groups,Y hydrogen, nitro, halogen, cyano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,OR¹, S(O)_(n)R², SO₂N(R¹)₂, N(R¹)₂, NR¹SO₂R², NR¹COR¹,(C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²,(C₁-C₆)-alkylphenyl, (C₁-C₆)-alkylheteroaryl, (C₁-C₆)-alkylheterocyclyl,phenyl, heteroaryl or heterocyclyl, where the 6 last-mentioned radicalsare each substituted by s radicals from the group consisting of halogen,nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, and where heterocyclylcarries 0 to 2 oxo groups,Z represents halogen, cyano, nitro, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, S(O)_(n)R², 1,2,4-triazol-1-yl,or Z may also represent hydrogen if Y represents the S(O)_(n)R² radical,V represents hydrogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, S(O)_(n)—(C₁-C₆)-alkyl,S(O)_(n)—(C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, halogen, nitroor cyano,R represents hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl,halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,cyano-(C₁-C₆)-alkyl, cyano, methylsulfenyl, methylsulfinyl,methylsulfonyl, acetylamino, halogen, amino, methoxymethyl,R¹ represents hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl,(C₁-C₆)-alkylheteroaryl, heterocyclyl, (C₁-C₆)-alkylheterocyclyl,(C₁-C₆)-alkyl-O-heteroaryl, (C₁-C₆)-alkyl-O-heterocyclyl,(C₁-C₆)-alkyl-NR³-heteroaryl or (C₁-C₆)-alkyl-NR³-heterocyclyl, wherethe 16 last-mentioned radicals are substituted by s radicals from thegroup consisting of cyano, halogen, nitro, OR³, S(O)_(n)R⁴, N(R³)₂,NR³OR³, COR³, OCOR³, NR³COR³, NR³SO₂R⁴, CO₂R³, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries 0to 2 oxo groups,R² represents (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl or(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, where these three radicals mentionedabove are each substituted by s radicals from the group consisting ofhalogen and OR³,R³ represents hydrogen or (C₁-C₆)-alkyl,R⁴ represents (C₁-C₆)-alkyl,R⁶ and R⁷ independently of one another each represent methyl, ethyl orn-propyl, orR⁶ and R⁷ together with the sulfur atom to which they are attached forma 5- or 6-membered saturated ring which, in addition to the carbon atomsand in addition to the sulfur atom of the sulfoximino group, contains moxygen atoms,R⁸ represents methyl, ethyl or n-propyl,R⁹ represents hydrogen or cyano,m represents 0 or 1,n represents 0, 1 or 2,s represents 0, 1, 2 or 3,except for compounds in which R and Y each represent hydrogen and at thesame timea) Z represents fluorine and X represents nitro, bromine or chlorine, orb) Z represents chlorine and X represents chlorine, orc) Z represents methoxy and X represents methoxy, ord) Z represents ethoxy and X represents ethoxy, ore) Z represents methyl sulfide and X represents methoxy.

In all the formulae specified hereinafter, the substituents and symbolshave the same meaning as described in formula (I), unless defineddifferently.

Compounds according to the invention can be prepared, for example, bythe method shown in scheme 1, by base-catalyzed reaction of a benzoylchloride (II) with a 3-aminoisoxazole (III):

Compounds according to the invention can also be prepared by the methoddescribed in scheme 2, by reacting a benzoic acid of the formula (IV)with a 3-aminoisoxazole (III):

For the activation, it is possible to use dehydrating reagents which aretypically for amidation reactions, for example 1,1′-carbonyldiimidazole(CDI), dicyclohexylcarbodiimide (DCC),2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P),etc.

It may be expedient to change the order of reaction steps. Thus, benzoicacids carrying a sulfoxide cannot be converted directly into their acidchlorides. Here, it is advisable to prepare initially, at the thioetherstage, the amide and then to oxidize the thioether to the sulfoxide.

The benzoyl chlorides of the formula (II) or the parent benzoic acidsthereof (IV) are known in principle and can be prepared, for example, bythe methods described in U.S. Pat. No. 6,376,429 B1, EP 1 585 742 A1 andEP 1 202 978 A1.

The 3-aminoisoxazoles of the formula (III) are either commerciallyavailable or can be prepared analogously to methods known from theliterature.

For example, 3-amino-4-R-isoxazoles can be prepared by the methoddescribed in Monatshefte für Chemie 1970, 101 (4), p. 1109, from asubstituted acrylonitrile (V):

In the abovementioned formula, R is, for example, an alkyl radical.3-Aminoisoxazoles of the formula (III) in which R represents halogen canbe prepared, for example, as described in WO2010/68453 by halogenationof 3-aminoisoxazole (VI) using customary halogenating agents such as,for example, Cl₂, Br₂ or N-halosuccinimides:

Collections of compounds of the formula (I) and/or salts thereof whichcan be synthesized by the abovementioned reactions can also be preparedin a parallelized manner, in which case this may be accomplished in amanual, partly automated or fully automated manner. It is possible, forexample, to automate the conduct of the reaction, the work-up or thepurification of the products and/or intermediates. Overall, this isunderstood to mean a procedure as described, for example, by D. Tiebesin Combinatorial Chemistry—Synthesis, Analysis, Screening (editorGünther Jung), Wiley, 1999, on pages 1 to 34.

For the parallelized conduct of the reaction and workup, it is possibleto use a number of commercially available instruments, for exampleCalypso reaction blocks from Barnstead International, Dubuque, Iowa52004-0797, USA or reaction stations from Radleys, Shirehill, SaffronWalden, Essex, CB11 3AZ, England, or MuItiPROBE Automated Workstationsfrom PerkinElmer, Waltham, Mass. 02451, USA. For the parallelizedpurification of compounds of the general formula (I) and salts thereofor of intermediates which occur in the course of preparation, availableapparatuses include chromatography apparatuses, for example from ISCO,Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA.

The apparatuses detailed lead to a modular procedure in which theindividual working steps are automated, but manual operations have to becarried out between the working steps. This can be circumvented by usingpartly or fully integrated automation systems in which the respectiveautomation modules are operated, for example, by robots. Automationsystems of this type can be obtained, for example, from Caliper,Hopkinton, Mass. 01748, USA.

The implementation of single or multiple synthesis steps can besupported by the use of polymer-supported reagents/scavenger resins. Thespecialist literature describes a series of experimental protocols, forexample in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers andReagents for Solution-Phase Synthesis (Sigma-Aldrich).

Aside from the methods described here, compounds of the general formula(I) and salts thereof can be prepared completely or partially bysolid-phase-supported methods. For this purpose, individualintermediates or all intermediates in the synthesis or a synthesisadapted for the corresponding procedure are bound to a synthesis resin.Solid-phase-supported synthesis methods are described adequately in thetechnical literature, for example Barry A. Bunin in “The CombinatorialIndex”, Academic Press, 1998 and Combinatorial Chemistry Synthesis,Analysis, Screening (editor: Günther Jung), Wiley, 1999. The use ofsolid-phase-supported synthesis methods permits a number of protocols,which are known from the literature and which for their part may beperformed manually or in an automated manner. The reactions can beperformed, for example, by means of IRORI technology in microreactorsfrom Nexus Biosystems, 12140 Community Road, Poway, Calif. 92064, USA.

Both in the solid and in the liquid phase, individual or severalsynthesis steps may be supported by the use of microwave technology. Thespecialist literature describes a series of experimental protocols, forexample in Microwaves in Organic and Medicinal Chemistry (editor: C. O.Kappe and A. Stadler), Wiley, 2005.

The preparation by the processes described here gives compounds of theformula (I) and salts thereof in the form of substance collections,which are called libraries. The present invention also provideslibraries comprising at least two compounds of the formula (I) and saltsthereof.

The compounds of the formula (I) according to the invention (and/orsalts thereof), referred to collectively as “compounds according to theinvention” hereinafter, have excellent herbicidal efficacy against abroad spectrum of economically important monocotyledonous anddicotyledonous annual harmful plants. The active compounds also havegood control over perennial harmful plants which are difficult tocontrol and produce shoots from rhizomes, root stocks or other perennialorgans.

The present invention therefore also provides a method for controllingunwanted plants or for regulating the growth of plants, preferably inplant crops, in which one or more compound(s) according to the inventionis/are applied to the plants (for example harmful plants such asmonocotyledonous or dicotyledonous weeds or unwanted crop plants), theseed (for example grains, seeds or vegetative propagules such as tubersor shoot parts with buds) or the area on which the plants grow (forexample the area under cultivation). The compounds according to theinvention can be deployed, for example, prior to sowing (if appropriatealso by incorporation into the soil), prior to emergence or afteremergence. Specific examples of some representatives of themonocotyledonous and dicotyledonous weed flora which can be controlledby the compounds according to the invention are as follows, though theenumeration is not intended to impose a restriction to particularspecies.

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron,Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus,Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa,Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis,Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria,Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,Scirpus, Setaria, Sorghum.

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella,Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura,Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium,Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria,Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago,Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex,Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

If the compounds according to the invention are applied to the soilsurface before germination, either the emergence of the weed seedlingsis prevented completely or the weeds grow until they have reached thecotyledon stage, but then they stop growing and ultimately diecompletely after three to four weeks have passed.

If the active compounds are applied post-emergence to the green parts ofthe plants, growth stops after the treatment, and the harmful plantsremain at the growth stage of the time of application, or they diecompletely after a certain time, such that competition by the weeds,which is harmful to the crop plants, is thus eliminated very early andin a lasting manner.

Although the compounds according to the invention have outstandingherbicidal activity against monocotyledonous and dicotyledonous weeds,crop plants of economically important crops, for example dicotyledonouscrops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita,Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum,Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, ormonocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea, in particular Zea and Triticum, will be damaged to anegligible extent only, if at all, depending on the structure of theparticular compound according to the invention and its application rate.For these reasons, the present compounds are very suitable for selectivecontrol of unwanted plant growth in plant crops such as agriculturallyuseful plants or ornamental plants.

In addition, the compounds according to the invention (depending ontheir particular structure and the application rate deployed) haveoutstanding growth-regulating properties in crop plants. They intervenein the plants' own metabolism with regulatory effect, and can thus beused for controlled influencing of plant constituents and to facilitateharvesting, for example by triggering desiccation and stunted growth. Inaddition, they are also suitable for general control and inhibition ofunwanted vegetative growth without killing the plants. Inhibition ofvegetative growth plays a major role for many mono- and dicotyledonousplants since, for example, this can reduce or completely preventlodging.

By virtue of their herbicidal and plant growth regulatory properties,the active compounds can also be used to control harmful plants in cropsof genetically modified plants or plants modified by conventionalmutagenesis. In general, transgenic plants are notable for particularadvantageous properties, for example for resistances to certainpesticides, in particular certain herbicides, resistances to plantdiseases or pathogens of plant diseases, such as certain insects ormicroorganisms such as fungi, bacteria or viruses. Other particularproperties relate, for example, to the harvested material with regard toquantity, quality, storability, composition and specific constituents.For instance, there are known transgenic plants with an elevated starchcontent or altered starch quality, or with a different fatty acidcomposition in the harvested material.

It is preferable, with respect to transgenic crops, to use the compoundsaccording to the invention in economically important transgenic crops ofuseful plants and ornamentals, for example of cereals such as wheat,barley, rye, oats, millet/sorghum, rice and corn or else crops of sugarbeet, cotton, soybean, oilseed rape, potato, tomato, peas and othertypes of vegetable. It is preferred to employ the compounds according tothe invention as herbicides in crops of useful plants which areresistant, or have been made resistant by recombinant means, to thephytotoxic effects of the herbicides.

Preference is given to the use of the compounds according to theinvention or salts thereof in economically important transgenic crops ofuseful plants and ornamentals, for example of cereals such as wheat,barley, rye, oats, millet/sorghum, rice, cassava and corn, or else cropsof sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas andother types of vegetable. Preferably, the compounds according to theinvention can be used as herbicides in crops of useful plants which areresistant, or have been made resistant by genetic engineering, to thephytotoxic effects of the herbicides.

Conventional ways of producing novel plants which have modifiedproperties in comparison to plants which have occurred to date consist,for example, in traditional breeding methods and the generation ofmutants. Alternatively, novel plants with altered properties can begenerated with the aid of recombinant methods (see, for example,EP-A-0221044, EP-A-0131624). For example, there have been descriptionsin several cases of:

-   -   genetic modifications of crop plants for the purpose of        modifying the starch synthesized in the plants (e.g. WO        92/11376, WO 92/14827, WO 91/19806),    -   transgenic crop plants which are resistant to particular        herbicides of the glufosinate type (cf., for example,        EP-A-0242236, EP-A-242246) or glyphosate type (WO 92/00377) or        of the sulfonylureas (EP-A-0257993, USA 5013659),    -   transgenic crop plants, for example cotton, capable of producing        Bacillus thuringiensis toxins (Bt toxins), which make the plants        resistant to particular pests (EP-A-0142924, EP-A-0193259),    -   transgenic crop plants with a modified fatty acid composition        (WO 91/13972),    -   genetically modified crop plants with novel constituents or        secondary metabolites, for example novel phytoalexins, which        bring about an increased disease resistance (EPA 309862,        EPA0464461),    -   genetically modified plants having reduced photorespiration,        which have higher yields and higher stress tolerance (EPA        0305398),    -   transgenic crop plants which produce pharmaceutically or        diagnostically important proteins (“molecular pharming”),    -   transgenic crop plants which feature higher yields or better        quality,    -   transgenic crop plants which feature a combination, for example,        of the abovementioned novel properties (“gene stacking”).

A large number of molecular-biological techniques by means of whichnovel transgenic plants with modified properties can be generated areknown in principle; see, for example, I. Potrykus and G. Spangenberg(eds.) Gene Transfer to Plants, Springer Lab Manual (1995), SpringerVerlag Berlin, Heidelberg, or Christou, “Trends in Plant Science” 1(1996) 423-431.

For such recombinant manipulations, nucleic acid molecules which allowmutagenesis or sequence alteration by recombination of DNA sequences canbe introduced into plasmids. With the aid of standard methods, it ispossible, for example, to undertake base exchanges, remove parts ofsequences or add natural or synthetic sequences. For the joining of theDNA fragments to one another, adaptors or linkers can be attached to thefragments; see, for example, Sambrook et al., 1989, Molecular Cloning, ALaboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, ColdSpring Harbor, N.Y.; or Winnacker “Gene and Klone” [Genes and Clones],VCH Weinheim 2nd edition 1996.

For example, the generation of plant cells with a reduced activity of agene product can be achieved by expressing at least one correspondingantisense RNA, a sense RNA for achieving a cosuppression effect, or byexpressing at least one suitably constructed ribozyme which specificallycleaves transcripts of the abovementioned gene product. To this end, itis firstly possible to use DNA molecules which encompass the entirecoding sequence of a gene product inclusive of any flanking sequenceswhich may be present, and also DNA molecules which only encompassportions of the coding sequence, in which case it is necessary for theseportions to be long enough to have an antisense effect in the cells. Itis also possible to use DNA sequences which have a high degree ofhomology to the coding sequences of a gene product, but are notcompletely identical to them.

When expressing nucleic acid molecules in plants, the proteinsynthesized may be localized in any desired compartment of the plantcell. However, to achieve localization in a particular compartment, itis possible, for example, to join the coding region to DNA sequenceswhich ensure localization in a particular compartment. Such sequencesare known to those skilled in the art (see, for example, Braun et al.,EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA85 (1988), 846-850, Sonnewald et al., Plant J. 1 (1991), 95-106). Thenucleic acid molecules can also be expressed in the organelles of theplant cells.

The transgenic plant cells can be regenerated by known techniques togive rise to entire plants. In principle, the transgenic plants may beplants of any desired plant species, i.e. not only monocotyledonous butalso dicotyledonous plants.

Thus, transgenic plants can be obtained whose properties are altered byoverexpression, suppression or inhibition of homologous (=natural) genesor gene sequences or expression of heterologous (=foreign) genes or genesequences.

The compounds according to the invention can be used with preference intransgenic crops which are resistant to growth regulators, for exampledicamba, or to herbicides which inhibit essential plant enzymes, forexample acetolactate synthases (ALS), EPSP synthases, glutaminesynthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or toherbicides from the group of the sulfonylureas, the glyphosates,glufosinates or benzoylisoxazoles and analogous active compounds.

When the active compounds according to the invention are used intransgenic crops, not only do the effects toward harmful plants whichare observed in other crops occur, but often also effects which arespecific to application in the particular transgenic crop, for examplean altered or specifically widened spectrum of weeds which can becontrolled, altered application rates which can be used for theapplication, preferably good combinability with the herbicides to whichthe transgenic crop is resistant, and influencing of growth and yield ofthe transgenic crop plants.

The invention therefore also provides for the use of the compoundsaccording to the invention as herbicides for control of harmful plantsin transgenic crop plants.

The compounds according to the invention can be applied in the form ofwettable powders, emulsifiable concentrates, sprayable solutions,dusting products or granules in the customary formulations. Theinvention therefore also provides herbicidal and plant-growth-regulatingcompositions which comprise the compounds according to the invention.

The compounds according to the invention can be formulated in variousways, according to the biological and/or physicochemical parametersrequired. Possible formulations include, for example: wettable powders(WP), water-soluble powders (SP), water-soluble concentrates,emulsifiable concentrates (EC), emulsions (EW) such as oil-in-water andwater-in-oil emulsions, sprayable solutions, suspension concentrates(SC), oil- or water-based dispersions, oil-miscible solutions, capsulesuspensions (CS), dusting products (DP), seed-dressing products,granules for scattering and soil application, granules (GR) in the formof microgranules, spray granules, coated granules and adsorptiongranules, water-dispersible granules (WG), water-soluble granules (SG),ULV formulations, microcapsules and waxes.

These individual types of formulation are known in principle and aredescribed, for example, in: Winnacker-Küchler, “Chemische Technologie”[Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th ed. 1986;Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y.,1973; K. Martens, “Spray Drying” Handbook, 3rd ed. 1979, G. Goodwin Ltd.London.

The formulation auxiliaries required, such as inert materials,surfactants, solvents and further additives, are likewise known and aredescribed, for example, in: Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd ed., Darland Books, Caldwell N.J.; H. v.Olphen, “Introduction to Clay Colloid Chemistry”, 2nd ed., J. Wiley &Sons, N.Y.; C. Marsden, “Solvents Guide”, 2nd ed., Interscience, N.Y.1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt,“Grenzflächenaktive Äthylenoxidaddukte” [Interface-active Ethylene OxideAdducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler,“Chemische Technologie” [Chemical Engineering], volume 7, C. HanserVerlag Munich, 4th ed. 1986.

On the basis of these formulations, it is also possible to producecombinations with other pesticidally active substances, for exampleinsecticides, acaricides, herbicides, fungicides, and also withsafeners, fertilizers and/or growth regulators, for example in the formof a finished formulation or as a tankmix. Suitable safeners are, forexample, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl,cloquintocet-mexyl and dichlormid.

Wettable powders are preparations which can be dispersed uniformly inwater and, in addition to the active compound, apart from a diluent orinert substance, also comprise surfactants of the ionic and/or nonionictype (wetting agents, dispersants), for example polyoxyethylatedalkylphenols, polyoxyethlated fatty alcohols, polyoxyethylated fattyamines, fatty alcohol polyglycol ether sulfates, alkanesulfonates,alkylbenzenesulfonates, sodium lignosulfonate, sodium2,2′-dinaphthylmethane-6,6′-disulfonate, sodiumdibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate. Toproduce the wettable powders, the herbicidally active compounds arefinely ground, for example in customary apparatus such as hammer mills,blower mills and air-jet mills, and simultaneously or subsequently mixedwith the formulation auxiliaries.

Emulsifiable concentrates are produced by dissolving the active compoundin an organic solvent, for example butanol, cyclohexanone,dimethylformamide, xylene, or else relatively high-boiling aromatics orhydrocarbons or mixtures of the organic solvents, with addition of oneor more ionic and/or nonionic surfactants (emulsifiers). Examples ofemulsifiers which may be used are: calcium alkylarylsulfonate salts suchas calcium dodecylbenzenesulfonate, or nonionic emulsifiers such asfatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcoholpolyglycol ethers, propylene oxide-ethylene oxide condensation products,alkyl polyethers, sorbitan esters, for example sorbitan fatty acidesters, or polyoxyethylene sorbitan esters, for example polyoxyethylenesorbitan fatty acid esters.

Dustable powders are obtained by grinding the active compound withfinely distributed solid substances, for example talc, natural clayssuch as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water- or oil-based. They may beprepared, for example, by wet-grinding by means of commercial bead millsand optional addition of surfactants as have, for example, already beenlisted above for the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be produced, forexample, by means of stirrers, colloid mills and/or static mixers usingaqueous organic solvents and optionally surfactants as already listedabove, for example, for the other formulation types.

Granules can be prepared either by spraying the active compound ontoadsorptive granular inert material or by applying active compoundconcentrates to the surface of carriers, such as sand, kaolinites orgranular inert material, by means of adhesives, for example polyvinylalcohol, sodium polyacrylate or else mineral oils. Suitable activecompounds can also be granulated in the manner customary for theproduction of fertilizer granules—if desired as a mixture withfertilizers.

Water-dispersible granules are produced generally by the customaryprocesses such as spray-drying, fluidized bed granulation, pangranulation, mixing with high-speed mixers and extrusion without solidinert material.

For the production of pan granules, fluidized bed granules, extrudergranules and spray granules, see, for example, processes in“Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London, J. E.Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff.;“Perry's Chemical Engineer's Handbook”, 5th ed., McGraw-Hill, New York1973, pp. 8-57.

For further details regarding the formulation of crop protectioncompositions, see, for example, G. C. Klingman, “Weed Control as aScience”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J.D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th ed., BlackwellScientific Publications, Oxford, 1968, pages 101-103.

The agrochemical preparations contain generally 0.1 to 99% by weight,especially 0.1 to 95% by weight, of compounds according to theinvention.

In wettable powders, the active compound concentration is, for example,about 10 to 90% by weight, the remainder to 100% by weight consisting ofcustomary formulation constituents. In emulsifiable concentrates, theactive compound concentration may be about 1 to 90% and preferably 5 to80% by weight. Dust-type formulations contain 1% to 30% by weight ofactive compound, preferably usually 5% to 20% by weight of activecompound; sprayable solutions contain about 0.05% to 80% by weight,preferably 2% to 50% by weight of active compound. In the case ofwater-dispersible granules, the active compound content dependspartially on whether the active compound is present in liquid or solidform and on which granulation auxiliaries, fillers, etc., are used. Inthe water-dispersible granules, the content of active compound is, forexample, between 1 and 95% by weight, preferably between 10 and 80% byweight.

In addition, the active compound formulations mentioned optionallycomprise the respective customary stickers, wetters, dispersants,emulsifiers, penetrants, preservatives, antifreeze agents and solvents,fillers, carriers and dyes, defoamers, evaporation inhibitors and agentswhich influence the pH and the viscosity.

On the basis of these formulations, it is also possible to producecombinations with other pesticidally active substances, for exampleinsecticides, acaricides, herbicides, fungicides, and also withsafeners, fertilizers and/or growth regulators, for example in the formof a finished formulation or as a tankmix.

For application, the formulations in commercial form are, ifappropriate, diluted in a customary manner, for example in the case ofwettable powders, emulsifiable concentrates, dispersions andwater-dispersible granules with water. Dust-type formulations, granulesfor soil application or granules for scattering and sprayable solutionsare not normally diluted further with other inert substances prior toapplication.

The required application rate of the compounds of the formula (I) varieswith the external conditions, including temperature, humidity and thetype of herbicide used. It can vary within wide limits, for examplebetween 0.001 and 1.0 kg/ha or more of active substance, but it ispreferably between 0.005 and 750 g/ha.

The examples which follow illustrate the invention.

A. CHEMICAL EXAMPLES Synthesis of2,4-difluoro-N-(1,2-oxazol-3-yl)benzamide (Table example 1-1)

At 0-5° C., 346 mg (1.96 mmol) of 2,4-difluorobenzoyl chloride are addedto a solution of 150 mg (1.78 mmol) of 1,2-oxazole-3-amine and 11 mg(0.089 mmol) of 4-dimethylaminopyridine in 5 ml of dichloromethane. Thereaction mixture is stirred at 5° C. for 3 h and then overnight at roomtemperature. 5 ml of water are then added, and the mixture is extractedthree times with 5 ml of dichloromethane each time. The combined organicphases are dried over magnesium sulfate, filtered and concentrated. Theresidue is purified by column chromatography (silica gel, heptane, ethylacetate). Yield 233 mg (57%).

¹H-NMR, DMSO-d₆, 400 MHz: 11.49 (s, 1H), 8.87 (s, 1H), 7.79 (ddd, 1H),7.42 (td, 1H), 7.22 (td, 1H), 7.01 (s, 1H).

Synthesis of2-chloro-4-(methylsulfonyl)-N-(1,2-oxazol-3-yl)-3-[(2,2,2-trifluoroethoxy)methyl]benzamide,(Table example No. 1-334)

825 mg (2.38 mmol) of2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoicacid and 200 mg (2.38 mmol) of 1,2-oxazole-3-amine are dissolved at roomtemperature (RT) in 20 ml of CH₂Cl₂, and 0.33 ml (2.38 mmol) oftriethylamine, 58 mg (0.48 mmol) of DMAP and 2.271 g (3.57 mmol) of2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50%solution in THF) are added. The reaction mixture is stirred at RT for 20h and then washed twice with in each case 10 ml of water. The organicphase is dried over Na₂SO₄ and concentrated. The residue is purified bycolumn chromatography (silica gel, heptane/ethyl acetate). Yield 240 mg(20%).

¹H-NMR, CDCl₃, 400 MHz: 9.50 (s, 1H), 8.32 (s, 1H), 8.22 (d, 1H), 7.79(d, 1H), 5.38 (s, 2H), 4.05 (q, 2H), 3.23 (s, 3H), 2.45 (s, 3H)

Synthesis of2-(methoxymethyl)-N-(1,2-oxazol-3-yl)-6-(trifluoromethyl)nicotinamide,(Table example No. 10-3)

118 mg (0.5 mmol) of 2-methoxymethyl-4-trifluoromethylnicotinic acid and42 mg (0.5 mmol) of 1,2-oxazole-3-amine are dissolved at RT in 10 ml ofCH₂Cl₂, and 0.5 ml (2.5 mmol) of triethylamine, 12 mg (0.1 mmol) of DMAPand 1.5 ml (7.5 mmol) of2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50%solution in THF) are added. The reaction mixture is stirred at RT for 20h and then washed twice with in each case 5 ml of water. The organicphase is dried over Na₂SO₄ and concentrated. The residue is purified bycolumn chromatography (silica gel, heptane/ethyl acetate). Yield 77 mg(51%).

¹H-NMR, DMSO-d₆, 400 MHz: 11.68 (s, 1H), 8.88 (s, 1H), 8.27 (d, 1H),8.00 (d, 1H), 7.05 (s, 1H), 4.71 (s, 2H), 3.23 (s, 3H).

Synthesis of2-chloro-N-[4-(2-cyanoethyl)-1,2-oxazol-3-yl]-3-[5-(cyanomethyl)-4,5-dihydro-1,2-oxazol-3-yl]-4-(ethylsulfonyl)benzamide,(Table example No. 9-343)

300 mg (0.84 mmol) of2-chloro-3-[5-(cyanomethyl)-4,5-dihydro-1,2-oxazol-3-yl]-4-(ethylsulfonyl)benzoicacid and 115 mg (0.84 mmol) of 3-(3-amino-1,2-oxazol-4-yl)propanonitrileare dissolved at RT in 20 ml of CH₂Cl₂, and 0.59 ml (4.20 mmol) oftriethylamine, 21 mg (0.168 mmol) of DMAP and 0.803 g (1.26 mmol) of2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50%solution in THF) are added. The reaction mixture is stirred at RT for 20h and then washed twice with in each case 10 ml of water. The organicphase is dried over Na₂SO₄ and concentrated. The residue is purified bycolumn chromatography (silica gel, heptane/ethyl acetate). Yield 230 mg(55%).

¹H-NMR, DMSO-d₆, 400 MHz: 11.23 (s, 1H), 8.88 (s, 1H), 8.11 (d, 1H),8.09 (d, 1H), 5.8 (m, 1H), 3.61 (dd, 1H), 3.41 (q, 2H), 3.30 (s, 3H),3.18 (dd, 1H), 3.01 (m, 2H), 2.81 (m, 4H), 1.15 (t, 3H).

Synthesis of 3-(3-amino-1,2-oxazol-4-yl)propanonitrile

At 0° C., 8.96 g (56.07 mmol) of bromine are slowly added dropwise to asolution of 7.0 g (65.96 mmol) of 2-methylenepentanedinitrile. Thereaction mixture is then stirred at 35° C. for 2 hours. The reactionmixture is then once more cooled to 0° C., and 6.52 g (85.75 mmol) of1-hydroxyurea are added. A solution of 7.13 g (178.09 mmol) of NaOH in15 ml of water is then slowly added dropwise at 0° C., and the mixtureis boiled under reflux for 3.5 hours. The solvents are concentrated andthe residue is then dissolved in 20 ml of water and extracted threetimes with in each case 10 ml of dichloromethane. The combined organicphases are dried over sodium sulfate and concentrated. Yield: 2.8 g(29%).

1H-NMR, DMSO-d₆, 400 MHz: 8.24 (s, 1H), 5.56 (bs, 2H), 2.71 (t, 2H),2.60 (t, 2H).

Synthesis of2-chloro-N-(4-methyl-1,2-oxazol-3-yl)-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzamide(Table example No. 2-334)

200 mg (0.58 mmol) of2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoicacid and 57 mg (0.58 mmol) of 4-methyl-1,2-oxazole-3-amine are dissolvedat RT in 24 ml of CH₂Cl₂, and 0.08 ml (0.58 mmol) of triethylamine, 14mg (0.12 mmol) of DMAP and 0.55 g (0.86 mmol) of2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50%solution in THF) are added. The reaction mixture is stirred at RT for 20h and then washed twice with in each case 10 ml of water. The organicphase is dried over Na₂SO₄ and concentrated. The residue is purified bycolumn chromatography (silica gel, heptane/ethyl acetate). Yield 150 mg(55%).

¹H-NMR, CDCl₃, 400 MHz: 8.56 (bs, 1H), 8.17 (s, 1H), 8.13 (d, 1H), 7.79(d, 1H), 5.36 (s, 2H), 4.08 (q, 2H), 3.21 (s, 3H), 2.12 (s, 3H).

Synthesis of 4-methyl-1,2-oxazole-3-amine

At 0° C., 4.05 g (25.34 mmol) of bromine are slowly added dropwise to asolution of 2.0 g (29.81 mmol) of methacrylonitrile. The mixture is thenstirred at 35° C. for 2 h. The mixture is then once more cooled to 0°C., and 2.95 g (38.75 mmol) of 1-hydroxyurea are added. A solution of3.22 g (80.49 mmol) of NaOH in 4 ml of water is then slowly addeddropwise at 0° C., and the mixture is boiled under reflux for 3.5 hours.The solvents are concentrated and the residue is then dissolved in 20 mlof water and extracted three times with in each case 10 ml ofdichloromethane. The combined organic phases are dried over sodiumsulfate, concentrated and purified on silica gel (heptane/ethylacetate). Yield: 0.7 g (24%).

¹H-NMR, DMSO-d₆, 400 MHz: 7.85 (s, 1H), 3.39 (bs, 2H), 1.92 (s, 3H).

2-Methyl-3-(methylsulfonyl)-4-(trifluoromethyl)-N-[4-(trifluoromethyl)-1,2-oxazol-3-yl]benzamide(Table example 7-173)

At 0° C., 129 mg (1.063 mmol) of thionyl chloride are added to asolution of 162 mg (1.063 mmol) of4-(trifluoromethyl)-1,2-oxazole-3-amine and 200 mg of2-methyl-3-methylsulfonyl-4-trifluoromethylbenzoic acid in 4 ml ofpyridine. The reaction mixture is stirred at 0° C. for 1 h and thenovernight at room temperature. The mixture is then concentrated. Theresidue is then dissolved in 5 ml of dichloromethane and extracted threetimes with in each case 5 ml of water. The combined organic phases aredried over magnesium sulfate, filtered and concentrated. The residue ispurified by column chromatography (HPLC, acetonitrile/water). Yield 233mg (57%).

¹H-NMR, DMSO-d₆, 400 MHz: 11.48 (s, 1H), 9.85 (s, 1H), 8.04 (d, 1H),7.90 (d, 1H), 3.43 (s, 3H), 2.73 (s, 3H)

Synthesis of 4-(trifluoromethyl)-1,2-oxazole-3-amine 1st Stage:Synthesis of 2-bromo-2-(bromomethyl)-3,3,3-trifluoropropanonitrile

To a solution of 30.4 g (190 mmol) of bromine in 100 ml of abs.chloroform are slowly added dropwise with stirring at 5° C. 23 g (190mmol) of 2-(trifluoromethyl)acrylonitrile. The reaction mixture is thenirradiated with a conventional laboratory lamp for 6 h. The red solutionis then concentrated. The residue (red oil, 43 g (81%) is used furtherin the next step, without further purification.

2nd Stage: Synthesis of 4-(trifluoromethyl)-1,2-oxazole-3-amine

At 5° C., 15 g (195 mmol) of 1-hydroxyurea are added to a solution of 42g (150 mmol) of 2-bromo-2-(bromomethyl)-3,3,3-trifluoropropanonitrile in120 ml of methanol. A 50% strength aqueous sodium hydroxide solution (31g; 0.39 mmol of NaOH) is then slowly added dropwise. After 4 hours ofstirring under reflux, the brown solution is poured onto 200 ml of waterand extracted three times with in each case 50 ml of ethyl acetate. Thecombined organic phases are washed with 20 ml of water, dried overmagnesium sulfate and concentrated. The residue is distilled underreduced pressure (b.p.: 50-55° C., 1 Torr) and then purified by columnchromatography (silica gel, methanol:chloroform 100:1). Yield: 4.4 g(19%)

¹H-NMR, CDCl₃: 8.41 (s, 1H); 4.2 (bs, 2H)

¹⁹F-NMR, CFCl₃, CDCl₃: −59.24 (s)

The compound 4-(trifluoromethyl)-1,2-oxazole-3-amine is novel and alsoforms part of the subject matter of the present invention.

The examples listed in the tables below were prepared analogously to theabovementioned methods or are obtainable analogously to theabovementioned methods. The compounds listed in the tables below arevery particularly preferred.

The abbreviations and terms used denote:

-   -   Et=ethyl Me=methyl n-Pr=n-propyl i-Pr=isopropyl    -   c-Pr=cyclopropyl Ph=phenyl Ac=acetyl t-Bu=tert-butyl

TABLE 1 Compounds of the general formula (I) according to the inventionin which R respresents H and A represents C—Y. (I)

Physical data (¹H-NMR, DMSO-d₆, 400 No. X Y Z V MHz) 1-1  F H F H 11.49(s, 1H), 8.87 (s, 1H), 7.79 (ddd, 1H), 7.42 (td, 1H), 7.22 (td, 1H),7.01 (s, 1H). 1-2  F H Cl H 1-3  F H SO₂Me H 1-4  F H SO₂Et H 1-5  F HCF₃ H 1-6  F H NO₂ H 1-7  Cl H F H 1-8  Cl H F F 1-9  Cl H Cl H 11.70(s, 1H), 8.87 (s, 1H), 7.78 (s, 1H), 7.78 (d, 1H), 7.56 (d, 1H), 7.02(s, 1H), 1-10  Cl H Br H 1-11  Cl H SMe H 1-12  Cl H SOMe H 1-13  Cl HSO₂Me H 11.84 (s, 1H), 8.89 (s, 1H), 8.11 (d, 1H), 7.99 (dd, 1H), 7.89(dd, 1H), 3.37 (s, 3H), 1-14  Cl H SO₂Et H 1-15  Cl H CF₃ H 1-16  Cl HNO₂ H 1-17  Cl H pyrazol-1-yl H 1-18  Br H Cl H 1-19  Br H Br H 1-20  BrH SO₂Me H 1-21  Br H SO₂Et H 1-22  Br H CF₃ H 1-23  SO₂Me H Cl H 1-24 SO₂Me H Br H 1-25  SO₂Me H SMe H 1-26  SO₂Me H SOMe H 1-27  SO₂Me HSO₂Me H 1-28  SO₂Me H SO₂Et H 1-29  SO₂Me H CF₃ H 11.90 (s, 1H), 8.27(d, 1H), 8.26 (s, 1H), 8.02 d, 1H), 7.01 (d, 1H), 3.45 (s, 3H). 1-30 SO₂Et H Cl H 1-31  SO₂Et H Br H 1-32  SO₂Et H SMe H 1-33  SO₂Et H SO₂MeH 1-34  SO₂Et H CF₃ H 1-35  CH₂SO₂Me H Br H 11.60 (s, 1H), 8.84 (d, 1H),7.79 (d, 1H), 7.75 (dd, 1H), 7.65 (dd, 1H), 6.99 (d, 1H), 2.33 (d, 3H),4.85 (s, 2H), 2.94 (s, 3H) 1-36  CH₂SO₂Me H CF₃ H 11.75 (s, 1H), 8.86(d, 1H), 7.95 (s, 1H), 7.91 (s, 2H), 7.02 (d, 1H), 4.94 (d, 3H), 2.97(s, 3H) 1-37  NO₂ H F H 1-38  NO₂ H Cl H 1-39  NO₂ H Br H 1-40  NO₂ H IH 1-41  NO₂ H CN H 1-42  NO₂ H SO₂Me H 11.95 (s, 1H), 8.91 (d, 1H), 8.63(d, 1H), 8.41 (dd, 1H), 8.09 (d, 1H), 7.03 (d, 1H), 3.42 (s, 3H) 1-43 NO₂ H SO₂Et H 1-44  NO₂ H CF₃ H 1-45  Me H F H 1-46  Me H Cl H 1-47  MeH Br H 1-48  Me H I H 1-49  Me H CN H 1-50  Me H SO₂Me H 1-51  Me HSO₂Et H 1-52  Me H CF₃ H 1-53  Et H F H 1-54  Et H Cl H 1-55  Et H Br H1-56  Et H I H 1-57  Et H CN H 1-58  Et H SO₂Me H 1-59  Et H SO₂Et H1-60  Et H CF₃ H 1-61  CF₃ H NO₂ H 1-62  CF₃ H Br H 1-63  CF₃ H CF₃ H1-64  CF₃ H SO₂Me H 1-65  CF₃ H SO₂Et H 1-66  CF₃ H Cl H 1-67  NO₂ NH₂ FH 1-68  NO₂ NHMe F H 1-69  NO₂ NMe₂ F H 1-70  NO₂ Me Cl H 1-71  NO₂ NH₂Cl H 1-72  NO₂ NHMe Cl H 1-73  NO₂ NMe₂ Cl H 1-74  NO₂ NH₂ Br H 1-75 NO₂ NHMe Br H 1-76  NO₂ NMe₂ Br H 1-77  NO₂ NH₂ CF₃ H 1-78  NO₂ NMe₂ CF₃H 1-79  NO₂ NH₂ SO₂Me H 1-80  NO₂ NH₂ SO₂Et H 1-81  NO₂ NHMe SO₂Me H1-82  NO₂ NMe₂ SO₂Me H 1-83  NO₂ NMe₂ SO₂Et H 1-84  NO₂ NH₂ 1H-1,2,4- Htriazol-1-yl 1-85  NO₂ NHMe 1H-1,2,4- H triazol-1-yl 1-86  NO₂ NMe₂1H-1,2,4- H triazol-1-yl 1-87  Me F F H 1-88  Me F Cl H 1-89  Me MeSO₂Me H 11.58 (s, 1H), 8.87 (d, 1H), 7.88 (d, 1H), 7.52 d, 1H), 7.05 (d,1H), 3.31 (s, 3H), 2.62 (s, 3H), 2.32 (s, 3H) 1-90  Me F SO₂Me H 11.70(s, 1H), 8.88 (s, 1H), 8.65 (s, 1H), 7.79 (t, 1H), 7.48 (d, 1H), 2.33(d, 3H), 1-91  Me Cl Cl H 1-92  Me O(CH₂)₂OMe Cl H 1-93  Me O(CH₂)₃OMeCl H 1-94  Me O(CH₂)₄OMe Cl H 1-95  Me OCH₂CONMe₂ Cl H 1-96  MeO(CH₂)₂—CO—NMe₂ Cl H 1-97  Me O(CH₂)₂—NH(CO)NMe₂ Cl H 1-98  MeO(CH₂)₂—NH(CO)NHCO₂Et Cl H 1-99  Me O(CH₂)₂—NHCO₂Me Cl H 1-100 MeOCH₂—NHSO₂cPr Cl H 1-101 Me O(CH₂)-5-2,4-dimethyl- Cl H2,4-dihydro-3H-1,2,4- triazol-3-one 1-102 Me O(CH₂)-3,5-dimethyl- Cl H1,2-oxazol-4-yl 1-103 Me OCH₂(CO)NMe₂ Br H 1-104 MeO(CH₂)-5-pyrrolidin-2- Br H one 1-105 Me Cl CF₃ H 1-106 Me Me SO₂Me H1-107 Me 4,5-dihydro-1,2-oxazol- SO₂Me H 3-yl 1-108 Me4,5-dihydro-1,2-oxazol- SO₂Et H 3-yl 1-109 Me 5-cyanomethyl-4,5- SO₂Me Hdihydro-1,2-oxazol-3-yl 1-110 Me 5-cyanomethyl-4,5- SO₂Et Hdihydro-1,2-oxazol-3-yl 1-111 Me NHCH₂C(O)NMe₂ SO₂Me H 1-112 Me SMe Me H1-113 Me SOMe Me H 1-114 Me SO₂Me Me H 1-115 Me SEt Me H 1-116 Me SOEtMe H 1-117 Me SO₂Et Me H 1-118 Me S(CH₂)₂OMe Me H 1-119 Me SO(CH₂)₂OMeMe H 1-120 Me SO₂(CH₂)₂OMe Me H 1-121 Me SO₂cPr Me H 1-122 Me OH SO₂Me H1-123 Me OMe SO₂Me H 1-124 Me OMe SO₂Et H 1-125 Me OEt SO₂Me H 1-126 MeOEt SO₂Et H 1-127 Me OiPr SO₂Me H 1-128 Me OiPr SO₂Et H 1-129 MeO(CH₂)₂OMe SO₂Me H 1-130 Me O(CH₂)₂OMe SO₂Et H 1-131 Me O(CH₂)₃OMe SO₂MeH 1-132 Me O(CH₂)₃OMe SO₂Et H 1-133 Me O(CH₂)₄OMe SO₂Me H 1-134 MeO(CH₂)₄OMe SO₂Et H 1-135 Me O(CH₂)₂NHSO₂Me SO₂Me H 1-136 MeO(CH₂)₂NHSO₂Me SO₂Et H 1-137 Me OCH₂(CO)NMe₂ SO₂Me H 1-138 MeOCH₂(CO)NMe₂ SO₂Et H 1-139 Me [1,4]dioxan-2-yl- SO₂Me H methoxy 1-140 Me[1,4]dioxan-2-yl- SO₂Et H methoxy 1-141 Me O(CH₂)₂—O-(3,5-di- SO₂Me Hmethoxypyrimidin-2-yl) 1-142 Me Cl SO₂Me H 11.72 (s, 1H), 8.89 (d, 1H),8.01 (d, 1H), 7.72 d, 1H), 7.05 (d, 1H), 3.43 (s, 3H), 2.44 (s, 3H)1-143 Me SMe H H 1-144 Me SOMe H H 1-145 Me SO₂Me H H 1-146 Me SEt H H1-147 Me SOEt H H 1-148 Me SO₂Et H H 1-149 Me S(CH₂)₂OMe H H 1-150 MeSO(CH₂)₂OMe H H 1-151 Me SO₂(CH₂)₂OMe H H 1-152 Me SMe F H 1-153 Me SOMeF H 1-154 Me SO₂Me F H 1-155 Me SEt F H 1-156 Me SOEt F H 1-157 Me SO₂EtF H 1-158 Me S(CH₂)₂OMe F H 1-159 Me SO(CH₂)₂OMe F H 1-160 MeSO₂(CH₂)₂OMe F H 1-161 Me SMe SO₂Me H 1-162 Me SOMe SO₂Me H 1-163 MeSO₂Me SO₂Me H 11.79 (s, 1H), 8.91 (d, 1H), 8.22 (d, 1H), 8.03 d, 1H),7.06 (d, 1H), 3.60 (s, 3H), 3.56 (s, 3H), 2.67 (s, 3H) 1-164 Me SO₂MeSO₂Et H 1-165 Me SEt SO₂Me H 1-166 Me SOEt SO₂Me H 1-167 Me SO₂Et SO₂MeH 1-168 Me S(CH₂)₂OMe SO₂Me H 1-169 Me SO(CH₂)₂OMe SO₂Me H 1-170 MeSO₂(CH₂)₂OMe SO₂Me H 1-171 Me SMe CF₃ H 11.60 (s, 1H), 8.89 (d, 1H),7.76 (d, 1H), 7.66 (d, 1H), 7.06 (d, 1H), 2.64 (s, 3H), 2.31 (s, 3H)1-172 Me SOMe CF₃ H 11.70 (s, 1H), 8.89 (d, 1H), 7.84 (d, 1H), 7.80 d,1H), 7.06 (d, 1H), 3.04 (s, 3H), 2.82 (s, 3H) 1-173 Me SO₂Me CF₃ H 11.76(s, 1H), 8.90 (d, 1H), 8.00 (d, 1H), 7.95 d, 1H), 7.06 (d, 1H), 3.41 (s,3H), 2.70 (s, 3H) 1-174 Me SEt CF₃ H 1-175 Me SOEt CF₃ H 1-176 Me SO₂EtCF₃ H 1-177 Me S(CH₂)₂OMe CF₃ H 1-178 Me SO(CH₂)₂OMe CF₃ H 1-179 MeSO₂(CH₂)₂OMe CF₃ H 1-180 Me SMe Br H 1-181 Me SOMe Br H 1-182 Me SO₂MeBr H 1-183 Me SEt Br H 1-184 Me SOEt Br H 1-185 Me SO₂Et Br H 1-186 MeSMe I H 1-187 Me SOMe I H 1-188 Me SO₂Me I H 1-189 Me SEt I H 1-190 MeSOEt I H 1-191 Me SO₂Et I H 1-192 Me SMe Cl H 1-193 Me SOMe Cl H 1-194Me SO₂Me Cl H 1-195 Me SEt Cl H 1-196 Me SOEt Cl H 1-197 Me SO₂Et Cl H1-198 Me S(CH₂)₂OMe Cl H 1-199 Me SO(CH₂)₂OMe Cl H 1-200 Me SO₂(CH₂)₂OMeCl H 1-201 CH₂SMe OMe SO₂Me H 1-202 CH₂OMe OMe SO₂Me H 1-203CH₂O(CH₂)₂OMe NH(CH₂)₂OEt SO₂Me H 1-204 CH₂O(CH₂)₂OMe NH(CH₂)₃OEt SO₂MeH 1-205 CH₂O(CH₂)₃OMe OMe SO₂Me H 1-206 CH₂O(CH₂)₂OMe NH(CH₂)₂OMe SO₂MeH 1-207 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me H 1-208 Et SMe Cl H 1-209 EtSOMe Cl H 1-210 Et SO₂Me Cl H 1-211 Et SMe CF₃ H 1-212 Et SOMe CF₃ H1-213 Et SO₂Me CF₃ H 1-214 Et F SO₂Me H 11.77 (s, 1H), 8.89 (d, 1H),7.81 (dd, 1H), 7.59 d, 1H), 7.05 (d, 1H), 3.44 (s, 3H), 2.77 (q, 2H),1.18 (t, 3H). 1-215 Et NH(CH₂)₂OMe SO₂Me H 1-216 iPr SMe CF₃ H 1-217 iPrSOMe CF₃ H 1-218 iPr SO₂Me CF₃ H 1-219 cPr SMe CF₃ H 1-220 cPr SOMe CF₃H 1-221 cPr SO₂Me CF₃ H 1-222 CF₃ O(CH₂)₂OMe F H 1-223 CF₃ O(CH₂)₃OMe FH 1-224 CF₃ OCH₂CONMe₂ F H 1-225 CF₃ [1,4]dioxan-2-yl- F H methoxy 1-226CF₃ O(CH₂)₂OMe Cl H 1-227 CF₃ O(CH₂)₃OMe Cl H 1-228 CF₃ OCH₂CONMe₂ Cl H1-229 CF₃ [1,4]dioxan-2- Cl H ylmethoxy 1-230 CF₃ O(CH₂)₂OMe Br H 1-231CF₃ O(CH₂)₃OMe Br H 1-232 CF₃ OCH₂CONMe₂ Br H 1-233 CF₃ [1,4]dioxan-2-Br H ylmethoxy 1-234 CF₃ O(CH₂)₂OMe I H 1-235 CF₃ O(CH₂)₃OMe I H 1-236CF₃ OCH₂CONMe₂ I H 1-237 CF₃ [1,4]dioxan-2- I H ylmethoxy 1-238 CF₃ FSO₂Me H 1-239 CF₃ F SO₂Et H 1-240 CF₃ O(CH₂)₂OMe SO₂Me H 1-241 CF₃O(CH₂)₂OMe SO₂Et H 1-242 CF₃ O(CH₂)₃OMe SO₂Me H 1-243 CF₃ O(CH₂)₃OMeSO₂Et H 1-244 CF₃ OCH₂CONMe₂ SO₂Me H 1-245 CF₃ OCH₂CONMe₂ SO₂Et H 1-246CF₃ [1,4]dioxan-2- SO₂Me H ylmethoxy 1-247 CF₃ [1,4]dioxan-2- SO₂Et Hylmethoxy 1-248 F SMe CF₃ H 11.78 (s, 1H), 8.87 (s, 1H), 7.81 (t, 1H),7.73 (d, 1H), 7.02 (s, 1H), 2.50 (s, 3H) 1-249 F SOMe CF₃ H 1-250 Cl MeSO₂Et H 11.75 (s, 1H), 8.89 (d, 1H), 7.97 (d, 1H), 7.70 d, 1H), 7.04 (d,1H), 3.40 (q, 2H), 2.73 (s, 3H), 1.13 (t, 3H) 1-251 Cl OCH₂CHCH₂ Cl H1-252 Cl OCH₂CHF₂ Cl H 1-253 Cl O(CH₂)₂OMe Cl H 1-254 Cl OCH₂CONMe₂ Cl H11.69 (s, 1H), 8.88 (d, 1H), 7.62 (d, 1H), 7.43 d, 1H), 7.02 (d, 1H),4.72 (s, 2H), 3.01 (s, 3H), 2.87 (s, 3H) 1-255 Cl O(CH₂)-5-pyrrolidin-2-Cl H one 1-256 Cl SMe H H 1-257 Cl SOMe H H 1-258 Cl SO₂Me H H 1-259 ClSEt H H 1-260 Cl SOEt H H 1-261 Cl SO₂Et H H 1-262 Cl S(CH₂)₂OMe H H1-263 Cl SO(CH₂)₂OMe H H 1-264 Cl SO₂(CH₂)₂OMe H H 1-265 Cl SMe Me H1-266 Cl SOMe Me H 1-267 Cl SO₂Me Me H 1-268 Cl SEt Me H 1-269 Cl SOEtMe H 1-270 Cl SO₂Et Me H 1-271 Cl S(CH₂)₂OMe Me H 1-272 Cl SO(CH₂)₂OMeMe H 1-273 Cl SO₂(CH₂)₂OMe Me H 1-274 Cl SMe F H 1-275 Cl SOMe F H 1-276Cl SO₂Me F H 1-277 Cl SEt F H 1-278 Cl SOEt F H 1-279 Cl SO₂Et F H 1-280Cl S(CH₂)₂OMe F H 1-281 Cl SO(CH₂)₂OMe F H 1-282 Cl SO₂(CH₂)₂OMe F H1-283 Cl SMe SO₂Me H 11.79 (s, 1H), 8.86 (s, 1H), 8.07 (d, 1H), 7.84 (d,1H), 7.04 (s, 1H), 3.57 (s, 3H), 3.50 (s, 3H) 1-284 Cl SOMe SO₂Me H11.88 (s, 1H), 8.92 (s, 1H), 8.10 (d, 1H), 8.01 (d, 1H), 7.06 (s, 1H),3.54 (s, 3H), 3.19 (s, 3H) 1-285 Cl SO₂Me SO₂Me H 11.91 (s, 1H), 8.92(s, 1H), 8.33 (d, 1H), 8.18 (d, 1H), 7.06 (s, 1H), 3.66 (s, 3H), 3.56(s, 3H) 1-286 Cl SO₂Me SO₂Et H 1-287 Cl SEt SO₂Me H 1-288 Cl SOEt SO₂MeH 1-289 Cl SO₂Et SO₂Me H 1-290 Cl S(CH₂)₂OMe SO₂Me H 1-291 ClSO(CH₂)₂OMe SO₂Me H 1-292 Cl SO₂(CH₂)₂OMe SO₂Me H 1-293 Cl SMe CF₃ H11.78 (s, 1H), 8.90 (s, 1H), 7.91 (d, 1H), 7.88 (d, 1H), 7.05 (s, 1H),2.44 (s, 3H) 1-294 Cl SOMe CF₃ H 11.87 (s, 1H), 8.92 (s, 1H), 8.02 (d,1H), 7.98 (d, 1H), 7.06 (s, 1H), 3.15 (s, 3H) 1-295 Cl SO₂Me CF₃ H 11.91(s, 1H), 8.92 (s, 1H), 8.16 (d, 1H), 8.13 (d, 1H), 7.06 (s, 1H), 3.52(s, 3H) 1-296 Cl SEt CF₃ H 1-297 Cl SOEt CF₃ H 1-298 Cl SO₂Et CF₃ H1-299 Cl S(CH₂)₂OMe CF₃ H 1-300 Cl SO(CH₂)₂OMe CF₃ H 1-301 ClSO₂(CH₂)₂OMe CF₃ H 1-302 Cl SMe Br H 1-303 Cl SOMe Br H 1-304 Cl SO₂MeBr H 1-305 Cl SEt Br H 1-306 Cl SOEt Br H 1-307 Cl SO₂Et Br H 1-308 ClSMe I H 1-309 Cl SOMe I H 1-310 Cl SO₂Me I H 1-311 Cl SEt I H 1-312 ClSOEt I H 1-313 Cl SO₂Et I H 1-314 Cl SMe Cl H 1-315 Cl SOMe Cl H 1-316Cl SO₂Me Cl H 1-317 Cl SEt Cl H 1-318 Cl SOEt Cl H 1-319 Cl SO₂Et Cl H1-320 Cl S(CH₂)₂OMe Cl H 1-321 Cl SO(CH₂)₂OMe Cl H 1-322 Cl SO₂(CH₂)₂OMeCl H 1-323 Cl F SMe H 1-324 Cl Cl SO₂Me H 11.86 (s, 1H), 8.91 (d, 1H),8.12 (d, 1H), 7.88 d, 1H), 7.05 (d, 1H), 3.47 (s, 3H) 1-325 Cl COOMeSO₂Me H 1-326 Cl CONMe₂ SO₂Me H 1-327 Cl CONMe(OMe) SO₂Me H 1-328 ClCH₂OMe SO₂Me H 1-329 Cl CH₂OMe SO₂Et H 1-330 Cl CH₂OEt SO₂Me H 1-331 ClCH₂OEt SO₂Et H 1-332 Cl CH₂OCH₂CH₂OMe SO₂Me H 1-333 Cl CH₂OCH₂CHF₂ SO₂MeH 1-334 Cl CH₂OCH₂CF₃ SO₂Me H 9.50 (s, 1H), 8.32 (s, 1H), 8.22 (d, 1H),7.79 (d, 1H), 5.38 (s, 2H), 4.05 (q, 2H), 3.23 (s, 3H), 2.45 (s, 3H)1-335 Cl CH₂OCH₂CF₃ SO₂Et H 1-336 Cl CH₂OCH₂CF₂CHF₂ SO₂Me H 1-337 ClCH₂OcPentyl SO₂Me H 1-338 Cl CH₂PO(OMe)₂ SO₂Me H 1-339 Cl4,5-dihydro-1,2-oxazol- SMe H 3-yl 1-340 Cl 4,5-dihydro-1,2-oxazol-SO₂Me H 3-yl 1-341 Cl 4,5-dihydro-1,2-oxazol- SO₂Et H 3-yl 1-342 Cl5-cyanomethyl-4,5- SO₂Me H dihydro-1,2-oxazol-3-yl 1-343 Cl5-cyanomethyl-4,5- SO₂Et H 11.85 (s, 1H), 8.91 (s, 1H),dihydro-1,2-oxazol-3-yl 8.09 (d, 1H), 8.04 (d, 1H), 7.05 (s, 1H), 5.19(m, 1H), 3.60 (dd, 1H), 3.42 (q, 2H), 3.14 (dd, 1H), 3.01 (m, 2H), 1.16(t, 3H). 1-344 Cl 5-(methoxymethyl)-4,5- SO₂Et H dihydro-1,2-oxazol-3-yl1-345 Cl 5-(methoxymethyl)-5- SO₂Et H methyl-4,5-dihydro-1,2-oxazol-3-yl 1-346 Cl CH₂O-tetrahydrofuran- SO₂Me H 3-yl 1-347 ClCH₂O-tetrahydrofuran- SO₂Et H 3-yl 1-348 Cl CH₂OCH₂- SO₂Me H 11.83 (s,1H), 8.89 (d, 1H), tetrahydrofuran-2-yl 8.07 (d, 1H), 7.86 d, 1H), 7.05(d, 1H), 5.08 (s, 2H), 3.99-3.94 (m, 1H), 3.73 (q, 1H), 3.69-3.55 (m,3H), 3.39 (s, 3H), 1.89-1.86 (m, 1H), 1.82-1.76 (m, 2H), 1.57-1.51 (m,1H) 1-349 Cl CH₂OCH₂- SO₂Et H tetrahydrofuran-2-yl 1-350 Cl CH₂OCH₂-SO₂Me H tetrahydrofuran-3-yl 1-351 Cl CH₂OCH₂- SO₂Et Htetrahydrofuran-3-yl 1-352 Cl OMe SO₂Me H 1-353 Cl OMe SO₂Et H 1-354 ClOEt SO₂Me H 1-355 Cl OEt SO₂Et H 1-356 Cl OiPr SO₂Me H 1-357 Cl OiPrSO₂Et H 1-358 Cl OnPr SO₂Me H 1-359 Cl O(CH₂)₂F SO₂Me H 1-360 ClO(CH₂)₂OMe SO₂Me H 1-361 Cl O(CH₂)₄OMe SO₂Me H 1-362 Cl O(CH₂)₄OMe SO₂EtH 1-363 Cl O(CH₂)₃OMe SO₂Me H 1-364 Cl O(CH₂)₂OMe SO₂Et H 1-365 ClO(CH₂)₂OMe SO₂Me H 1-366 Cl O(CH₂)₂OMe SO₂Et H 1-367 Cl OCH₂—c-Pr SO₂EtH 1-368 Cl [1,4]dioxan-2-yl- SO₂Me H methoxy 1-369 Cl [1,4]dioxan-2-yl-SO₂Et H methoxy 1-370 Cl OCH₂(CO)NMe₂ SO₂Me H 1-371 Cl OCH₂(CO)NMe₂SO₂Et H 1-372 Br OMe Br H 1-373 Br O(CH₂)₂OMe Br H 1-374 Br O(CH₂)₂OMeSO₂Me H 1-375 Br O(CH₂)₂OMe SO₂Et H 1-376 Br O(CH₂)₃OMe SO₂Me H 1-377 BrO(CH₂)₃OMe SO₂Et H 1-378 Br O(CH₂)₄OMe SO₂Me H 1-379 Br O(CH₂)₄OMe SO₂EtH 1-380 Br [1,4]dioxan-2- SO₂Me H ylmethoxy 1-381 Br [1,4]dioxan-2-SO₂Et H ylmethoxy 1-382 I O(CH₂)₂OMe SO₂Me H 1-383 I O(CH₂)₂OMe SO₂Et H1-384 I O(CH₂)₃OMe SO₂Me H 1-385 I O(CH₂)₃OMe SO₂Et H 1-386 I O(CH₂)₄OMeSO₂Me H 1-387 I O(CH₂)₄OMe SO₂Et H 1-388 I [1,4]dioxan-2- SO₂Me Hylmethoxy 1-389 I [1,4]dioxan-2- SO₂Et H ylmethoxy 1-390 OMe SMe CF₃ H1-391 OMe SOMe CF₃ H 1-392 OMe SO₂Me CF₃ H 1-393 OMe SEt CF₃ H 1-394 OMeSOEt CF₃ H 1-395 OMe SO₂Et CF₃ H 1-396 OMe S(CH₂)₂OMe CF₃ H 1-397 OMeSO(CH₂)₂OMe CF₃ H 1-398 OMe SO₂(CH₂)₂OMe CF₃ H 1-399 OMe SMe CHF₂ H1-400 OMe SOMe CHF₂ H 1-401 OMe SO₂Me CHF₂ H 1-402 OMe SEt CHF₂ H 1-403OMe SOEt CHF₂ H 1-404 OMe SO₂Et CHF₂ H 1-405 OMe S(CH₂)₂OMe CHF₂ H 1-406OMe SO(CH₂)₂OMe CHF₂ H 1-407 OMe SO₂(CH₂)₂OMe CHF₂ H 1-408 OMe SMe Cl H1-409 OMe SOMe Cl H 1-410 OMe SO₂Me Cl H 1-411 OMe SEt Cl H 1-412 OMeSOEt Cl H 1-413 OMe SO₂Et Cl H 1-414 OMe S(CH₂)₂OMe Cl H 1-415 OMeSO(CH₂)₂OMe Cl H 1-416 OMe SO₂(CH₂)₂OMe Cl H 1-417 OEt SMe CF₃ H 1-418OEt SOMe CF₃ H 1-419 OEt SO₂Me CF₃ H 1-420 OEt SEt CF₃ H 1-421 OEt SOEtCF₃ H 1-422 OEt SO₂Et CF₃ H 1-423 OEt S(CH₂)₂OMe CF₃ H 1-424 OEtSO(CH₂)₂OMe CF₃ H 1-425 OEt SO₂(CH₂)₂OMe CF₃ H 1-426 OEt SMe CHF₂ H1-427 OEt SOMe CHF₂ H 1-428 OEt SO₂Me CHF₂ H 1-429 OEt SEt CHF₂ H 1-430OEt SOEt CHF₂ H 1-431 OEt SO₂Et CHF₂ H 1-432 OEt S(CH₂)₂OMe CHF₂ H 1-433OEt SO(CH₂)₂OMe CHF₂ H 1-434 OEt SO₂(CH₂)₂OMe CHF₂ H 1-435 OEt SMe Cl H1-436 OEt SOMe Cl H 1-437 OEt SO₂Me Cl H 1-438 OEt SEt Cl H 1-439 OEtSOEt Cl H 1-440 OEt SO₂Et Cl H 1-441 OEt S(CH₂)₂OMe Cl H 1-442 OEtSO(CH₂)₂OMe Cl H 1-443 OEt SO₂(CH₂)₂OMe Cl H 1-444 O(CH₂)c-Pr SMe CF₃ H1-445 O(CH₂)c-Pr SOMe CF₃ H 1-446 O(CH₂)c-Pr SO₂Me CF₃ H 1-447O(CH₂)c-Pr SEt CF₃ H 1-448 O(CH₂)c-Pr SOEt CF₃ H 1-449 O(CH₂)c-Pr SO₂EtCF₃ H 1-450 O(CH₂)c-Pr S(CH₂)₂OMe CF₃ H 1-451 O(CH₂)c-Pr SO(CH₂)₂OMe CF₃H 1-452 O(CH₂)c-Pr SO₂(CH₂)₂OMe CF₃ H 1-453 O(CH₂)c-Pr SMe Cl H 1-454O(CH₂)c-Pr SOMe Cl H 1-455 O(CH₂)c-Pr SO₂Me Cl H 1-456 O(CH₂)c-Pr SEt ClH 1-457 O(CH₂)c-Pr SOEt Cl H 1-458 O(CH₂)c-Pr SO₂Et Cl H 1-459O(CH₂)c-Pr S(CH₂)₂OMe Cl H 1-460 O(CH₂)c-Pr SO(CH₂)₂OMe Cl H 1-461O(CH₂)c-Pr SO₂(CH₂)₂OMe Cl H 1-462 O(CH₂)c-Pr SMe SO₂Me H 1-463O(CH₂)c-Pr SOMe SO₂Me H 1-464 O(CH₂)c-Pr SO₂Me SO₂Me H 1-465 O(CH₂)c-PrSEt SO₂Me H 1-466 O(CH₂)c-Pr SOEt SO₂Me H 1-467 O(CH₂)c-Pr SO₂Et SO₂Me H1-468 O(CH₂)c-Pr S(CH₂)₂OMe SO₂Me H 1-469 O(CH₂)c-Pr SO(CH₂)₂OMe SO₂Me H1-470 O(CH₂)c-Pr SO₂(CH₂)₂OMe SO₂Me H 1-471 SO₂Me F CF₃ H 1-472 SO₂MeNH₂ CF₃ H 1-473 SO₂Me NHEt Cl H 1-474 SMe SEt F H 1-475 SMe SMe F H1-476 Me NH₂ Cl H 1-477 Me NHMe Cl H 1-478 Me NMe₂ Cl H 1-479 Mepyrazol-1-yl Cl H 1-480 Me NH₂ Br H 1-481 Me NHMe Br H 1-482 Me NMe₂ BrH 1-483 Me NH₂ SO₂Me H 1-484 Me NHMe SO₂Me H 1-485 Me NMe₂ SO₂Me H 1-486Me NH(CH₂)₂OMe SO₂Me H 1-487 Me morpholin-4-yl SO₂Me H 1-488 Me1,2,3-triazol-1-yl SO₂Me H 1-489 Me 1,2,3-triazol-2-yl SO₂Me H 11.85 (s,1H), 8.89 (d, 1H), 8.54 (s, 1H), 8.13 (d, 1H), 8.05 (s, 1H), 8.03 (d,1H), 7.06 (s, 1H), 3.13 (s, 3H), 1.88 (s, 3H) 1-490 Me pyrazol-1-ylSO₂Me H 1-491 Me 1,2,4-triazol-1-yl SO₂Me H 1-492 Me NH₂ CF₃ H 1-493 MeNHMe CF₃ H 1-494 Me NMe₂ CF₃ H 1-495 Me NH(CH₂)₂OMe CF₃ H 1-496 Memorpholin-4-yl CF₃ H 1-497 Me 1,2,3-triazol-1-yl CF₃ H 1-498 Me1,2,3-triazol-2-yl CF₃ H 1-499 Me pyrazol-1-yl CF₃ H 1-500 Me1,2,4-triazol-1-yl CF₃ H 1-501 Cl NH₂ Cl H 1-502 Cl NHMe Cl H 1-503 ClNMe₂ Cl H 1-504 Cl pyrazol-1-yl Cl H 1-505 Cl NH₂ Br H 1-506 Cl NHMe BrH 1-507 Cl NMe₂ Br H 1-508 Cl NH₂ SO₂Me H 1-509 Cl NHMe SO₂Me H 1-510 ClNMe₂ SO₂Me H 1-511 Cl NH(CH₂)₂OMe SO₂Me H 1-512 Cl morpholin-4-yl SO₂MeH 1-513 Cl 1,2,3-triazol-1-yl SO₂Me H 1-514 Cl 1,2,3-triazol-2-yl SO₂MeH 1-515 Cl pyrazol-1-yl SO₂Me H 1-516 Cl 1,2,4-triazol-1-yl SO₂Me H1-517 Cl NH₂ CF₃ H 1-518 Cl NHMe CF₃ H 1-519 Cl NMe₂ CF₃ H 1-520 ClNH(CH₂)₂OMe CF₃ H 1-521 Cl morpholin-4-yl CF₃ H 1-522 Cl1,2,3-triazol-1-yl CF₃ H 1-523 Cl 1,2,3-triazol-2-yl CF₃ H 1-524 Clpyrazol-1-yl CF₃ H 1-525 Cl 1,2,4-triazol-1-yl CF₃ H 1-526 Clsulfoximine 1 Cl H 1-527 Cl sulfoximine 2 Cl H 1-528 Cl sulfoximine 3 ClH 1-529 Cl sulfoximine 4 Cl H 1-530 Cl sulfoximine 5 Cl H 1-531 Clsulfoximine 3 OMe H 1-532 Cl sulfoximine 4 OMe H 1-533 Cl sulfoximine 5OMe H 1-534 Cl sulfoximine 3 COOMe H 1-535 Cl sulfoximine 4 COOMe H1-536 Cl sulfoximine 5 COOMe H 1-537 OMe sulfoximine 3 OMe H 1-538 OMesulfoximine 4 OMe H 1-539 OMe sulfoximine 5 OMe H 1-540 Me sulfoximine 1CF₃ H 1-541 Me sulfoximine 2 CF₃ H 1-542 Me sulfoximine 1 SO₂Me H 1-543Me sulfoximine 2 SO₂Me H 1-544 Me sulfoximine 1 Cl H 1-545 Mesulfoximine 2 Cl H 1-546 Cl H F F

TABLE 2 Compounds of the general formula (I) according to the inventionin which R represents methyl, A represents C—Y, and V, X, Y and Z havethe meanings given in Table 1.

Physical data (¹H-NMR, DMSO- No. X Y Z V d₆, 400 MHz) 2-13 Cl H SO₂Me H2-163 Me SO₂Me SO₂Me H 11.01 (s, 1H), 8.71 (s, 1H), 8.25 (d, 1H), 8.03(d, 1H), 3.60 (s, 3H), 3.56 (s, 3H), 2.72 (s, 3H), 1.99 (s, 3H) 2-172 MeSOMe CF₃ H 10.98 (s, 1H), 8.70 (s, 1H), 7.85 (d, 1H), 7.82 (d, 1H), 3.05(s, 3H), 2.87 (s, 3H), 2.01 (s, 3H) 2-173 Me SO₂Me CF₃ H 11.02 (s, 1H),8.71 (s, 1H), 8.02 (d, 1H), 7.96 (d, 1H), 3.42 (s, 3H), 2.75 (s, 3H),2.01 (s, 3H) 2-284 Cl SOMe SO₂Me H 11.14 (s, 1H), 8.71 (s, 1H), 8.11 (d,1H), 8.02 (d, 1H), 3.54 (s, 3H), 3.20 (s, 3H), 2.01 (s, 3H) 2-285 ClSO₂Me SO₂Me H 11.16 (s, 1H), 8.72 (s, 1H), 8.35 (d, 1H), 8.20 (d, 1H),3.66 (s, 3H), 3.57 (s, 3H), 2.01 (s, 3H) 2-293 Cl SMe CF₃ H 11.06 (s,1H), 8.71 (s, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 2.45 (s, 3H), 2.02 (s,3H) 2-294 Cl SOMe CF₃ H 11.14 (s, 1H), 8.71 (s, 1H), 8.03 (d, 1H), 7.99(d, 1H), 3.16 (s, 3H), 2.01 (s, 3H) 2-295 Cl SO₂Me CF₃ H 11.18 (s, 1H),8.72 (s, 1H), 8.16 (d, 1H), 8.14 (d, 1H), 3.53 (s, 3H), 2.02 (s, 3H)2-328 Cl CH₂OMe SO₂Me H 11.09 (s, 1H), 8.71 (s, 1H), 8.08 (d, 1H), 7.88(d, 1H), 4.98 (s, 1H), 3.42 (s, 3H), 3.36 (s, 3H), 2.00 (s, 3H). 2-334Cl CH₂OCH₂CF₃ SO₂Me H ¹H-NMR, CDCl₃, 400 MHz: 8.56 (bs, 1H), 8.17 (s,1H), 8.13 (d, 1H), 7.79 (d, 1H), 5.36 (s, 2H), 4.08 (q, 2H), 3.21 (s,3H), 2.12 (s, 3H). 2-343 Cl 5-cyanomethyl- SO₂Et H 11.18 (s, 1H), 8.74(s, 1H), 4,5-dihydro-1,2- 8.12 (d, 1H), 8.05 (d, 1H), oxazol-3-yl 5.19(m, 1H), 3.60 (dd, 1H), 3.41 (q, 2H), 3.15 (dd, 1H), 3.01 (m, 2H), 2.00(s, 3H), 1.17 (t, 3H). 2-390 Me SMe CF₃ H 10.86 (s, 1H), 8.70 (s, 1H),7.72 (d, 1H), 7.66 (d, 1H), 3.95 (s, 3H), 2.46 (s, 3H), 2.00 (s, 3H)

TABLE 3 Compounds of the general formula (I) accord- ing to theinvention in which R represents ethyl, A represents C—Y, and V, X, Y andZ have the meanings given in Table 1.

TABLE 4 Compounds of the general formula (I) accord- ing to theinvention in which R represents n- propyl, A represents C—Y, and V, X, Yand Z have the meanings given in Table 1.

TABLE 5 Compounds of the general formula (I) according to the inventionin which R represents isopropyl, A represents C—Y, and V, X, Y and Zhave the meanings given in Table 1.

Physical data (¹H-NMR, DMSO- No. X Y Z V d₆, 400 MHz) 5-163 Me SO₂MeSO₂Me H 10.92 (s, 1H), 8.76 (s, 1H), 8.26 (d, 1H), 7.99 (d, 1H), 3.59(s, 3H), 3.57 (s, 3H), 2.88-2.84 (m, 4H), 2.71 (s, 3H), 1.20 (d, 6H), ),5-172 Me SOMe CF₃ H 10.87 (s, 1H), 8.76 (s, 1H), 7.87 (d, 1H), 7.77 (d,1H), 3.05 (s, 3H), 2.91-2.84 (m, 4H), 1.20 (d, 6H), ), 5-173 Me SO₂MeCF₃ H 10.91 (s, 1H), 8.76 (s, 1H), 8.02 (d, 1H), 7.92 (d, 1H), 3.42 (s,3H), 2.88-2.83 (m, 1H), 2.75 (s, 3H), 1.20 (d, 6H) 5-343 Cl5-cyanomethyl- SO₂Et H 11.02 (s, 1H), 8.77 (s, 1H), 4,5-dihydro-1,2-8.12 (d, 1H), 8.00 (d, 1H), oxazol-3 yl 5.19 (m, 1H), 3.60 (dd, 1H),3.41 (q, 2H), 3.18 (dd, 1H), 3.01 (m, 2H), 2.88 (m, 1H), 1.19 (d, 6H).

TABLE 6 Compounds of the general formula (I) according to the inventionin which R represents t-butyl, A represents C—Y, and V, X, Y and Z havethe meanings given in Table 1.

Physical data (¹H-NMR, DMSO- No. X Y Z V d₆, 400 MHz) 6-172 Me SOMe CF₃H 10.54 (s, 1H), 8.79 (s, 1H), 7.89 (d, 1H), 7.71 (d, 1H), 2.89 (s, 3H),1.29 (s, 9H) 6-173 Me SO₂Me CF₃ H 10.58 (s, 1H), 8.79 (s, 1H), 8.04 (d,1H), 7.84 (d, 1H), 3.41 (s, 3H), 1.279 (s, 9H) 6-343 Cl 5-cyanomethyl-SO₂Et H 10.69 (s, 1H), 8.80 (s, 1H), 4,5-dihydro-1,2- 8.12 (d, 1H), 7.95(d, 1H), oxazol-3-yl 5.19 (m, 1H), 3.60 (dd, 1H), 3.41 (q, 2H), 3.18(dd, 1H), 3.01 (m, 2H), 1.30 (s, 9H), 1.15 (t, 3H).

TABLE 7 Compounds of the general formula (I) according to the inventionin which R represents trifluoromethyl, A represents C—Y, and V, X, Y andZ have the meanings given in Table 1.

Physical data (¹H-NMR, DMSO- No. X Y Z V d₆, 400 MHz) 7-173 Me SO₂Me CF₃H 11.48 (s, 1H), 9.85 (s, 1H), 8.04 (d, 1H), 7.90 (d, 1H), 3.43 (s, 3H),2.73 (s, 3H) 7-293 Cl SMe CF₃ H 11.49 (s, 1H), 9.83 (s, 1H), 7.94 (d,1H), 7.76 (d, 1H), 3.32 (s, 3H) 7-294 Cl SOMe CF₃ H 7-295 Cl SOMe CF₃ H11.60 (s, 1H), 9.84 (s, 1H), 8.17 (d, 1H), 8.06 (d, 1H), 3.54 (s, 3H)7-334 Cl CH₂OCH₂CF₃ SO₂Me H 11.55 (s, 1H), 9.84 (s, 1H), 8.12 (d, 1H),7.85 (d, 1H), 5.25 (s, 1H), 4.30 (q, 2H), 3.36 (s, 3H).

TABLE 8 Compounds of the general formula (I) according to the inventionin which R represents chlorine, A represents C—Y, and V, X, Y and Z havethe meanings given in Table 1.

Physical data (¹H-NMR, DMSO- No. X Y Z V d₆, 400 MHz) 8-173 Me SO₂Me CF₃H 11.30 (s, 1H), 9.35 (s, 1H), 8.03 (d, 1H), 7.95 (d, 1H), 3.43 (s, 3H),2.76 (s, 3H) 8-293 Cl SMe CF₃ H 11.31 (s, 1H), 9.34 (s, 1H), 7.93 (d,1H), 7.82 (d, 1H), 2.44 (s, 3H) 8-334 Cl CH₂OCH₂CF₃ SO₂Me H 11.38 (s,1H), 9.34 (s, 1H), 8.11 (d, 1H), 7.91 (d, 1H), 5.25 (s, 1H), 4.29 (q,2H), 3.37 (s, 3H).

TABLE 9 Compounds of the general formula (I) according to the inventionin which R represents CH₂CH₂CN, A represents C—Y, and V, X, Y and Z havethe meanings given in Table 1.

Physical data (¹H-NMR, DMSO- No. X Y Z V d₆, 400 MHz) 9-13 Cl H SO₂Me H11.20 (s, 1H), 8.87 (s, 1H), 8.14 (s, 1H), 8.00 (d, 1H), 7.96 (d, 1H),3.35 (s, 3H), 2.84-2.77 (m, 4H) 9-42 NO₂ H SO₂Me H 11.36 (s, 1H), 8.88(s, 1H), 8.65 (s, 1H), 8.42 (d, 1H), 8.13 (d, 1H), 3.42 (s, 3H),2.83-2.80 (m, 4H) 9-111 Me NHCH₂C(O)NMe₂ SO₂Me H 10.90 (s, 1H), 8.85 (s,1H), 7.64 (d, 1H), 7.27 (d, 1H), 6.30 (t, 1H), 4.05 (d, 1H), 3.20 (s,3H), 3.31 (s, 3H), 3.42 (s, 3H), 2.82-2.80 (m, 4H) 9-142 Me Cl SO₂Me H11.09 (s, 1H), 8.86 (s, 1H), 8.03 (d, 1H), 7.97 (d, 1H), 3.35 (s, 3H),2.85-2.76 (m, 4H), 2.28 (s, 3H), 2.50 (s, 3H) 9-172 Me SOMe CF₃ H 11.08(s, 1H), 8.86 (s, 1H), 7.86 (bs, 2H), 3.05 (s, 3H), 2.86 (s, 3H),2.85-2.77 (m, 4H) 9-238 CF₃ F CF₃ H 11.33 (s, 1H), 8.88 (s, 1H), 8.29(t, 1H), 7.88 (d, 1H), 3.31 (s, 3H), 2.84-2.74 (m, 4H), 9-250 Cl MeSO₂Et H 11.18 (s, 1H), 8.88 (s, 1H), 8.00 (d, 1H), 7.76 (d, 1H), 3.42(q, 2H), 2.84-2.78 (m, 4H) 9-324 Cl Cl SO₂Me H 11.24 (s, 1H), 8.88 (s,1H), 8.14 (s, 1H), 7.92 (d, 1H), 3.48 (s, 3H), 2.85-2.77 (m, 4H), 2.28(s, 3H), 1.13 (t, 3H) 9-334 Cl CH₂OCH₂CF₃ SO₂Me H 11.23 (s, 1H), 8.87(s, 1H), 7.97 (d, 1H), 7.88 (d, 1H), 5.26 (s, 2H), 4.29 (m, 2H), 3.36(s, 3H), 2.83-2.80 (m, 4H), 9-343 Cl 5-cyanomethyl- SO₂Et H 11.23 (s,1H), 8.88 (s, 4,5-dihydro-1,2- 1H), 8.11 (d, 1H), 8.09 oxazol-3-yl (d,1H), 5.18 (m, 1H), 3.61 (dd, 1H), 3.41 (q, 2H), 3.30 (s, 3H), 3.18 (dd,1H), 3.01 (m, 2H), 2.81 (m, 4H), 1.15 (t, 3H). 9-348 Cl CH₂OCH₂- SO₂Me H11.21 (s, 1H), 8.88 (s, 1H), tetrahydrofuran- 8.09 (d, 1H), 7.90 (d,1H), 2-yl 5.09 (s, 2H), 3.99-3.94 (m, 1H), 3.74-3.68 (m, 1H), 3.62-3.55(m, 3H), 3.33 (s, 3H), 2.83-2.79 (m, 4H), 1.92-1.75 (m, 3H), 1.59- 1.49(m, 1H),

TABLE 10 Compounds of the general formula (I) according to the inventionin which A represents N

Physical data (¹H-NMR, DMSO- No. R X Z V d₆, 400 MHz) 10-1 H Cl CF₃ H10.15 (s, 1H), 8.38 (s, 1H), 8.30 (d, 1H), 7.80 (d, 1H), 7.27 (s, 1H)10-2 H Me CF₃ H 11.76 (s, 1H), 8.90 (s, 1H), 8.22 (d, 1H), 7.88 (d, 1H),7.07 (s, 1H), 2.63 (s, 3H). 10-3 H CH₂OMe CF₃ H 11.68 (s, 1H), 8.88 (s,1H), 8.27 (d, 1H), 8.00 (d, 1H), 7.05 (s, 1H), 4.71 (s, 2H), 3.23 (s,3H). 10-4 H (1,1-dioxido-1,2- CF₃ H thiadiazolidin- 1-yl)methyl 10-5 HCH₂OCH₂CH₂OMe CF₃ H 10-6 H Cl Cl H 10-7 Me Cl CF₃ H 11.18 (s, 1H), 8.72(s, 1H), 8.45 (d, 1H), 8.14 (d, 1H), 2.01 (s, 3H) 10-8 Me Me CF₃ H 10-9Me CH₂OMe CF₃ H 10-10 Me (1,1-dioxido-1,2- CF₃ H 11.11 (s, 1H), 8.70thiadiazolidin- (s, 1H), 8.33 (d, 1-yl)methyl 1H), 8.02 (d, 1H), 4.50(s, 2H), 3.28 (t, 2H), 3.31 (t, 2H), 2.24-2.20 (m, 2H), 2.00 (s, 3H)10-11 Me CH₂OCH₂CH₂OMe CF₃ H 10-12 Me 10-13 Cl Cl CF₃ H 10-14 Cl Me CF₃H 10-15 Cl CH₂OMe CF₃ H 10-16 Cl (1,1-dioxido-1,2- CF₃ H thiadiazolidin-1-yl)methyl 10-17 Cl CH₂OCH₂CH₂OMe CF₃ H 10-18 Cl 10-19 CF₃ Cl CF₃ H10-20 CF₃ Me CF₃ H 10-21 CF₃ CH₂OMe CF₃ H 10-22 CF₃ (1,1-dioxido-1,2-CF₃ H thiadiazolidin- 1-yl)methyl 10-23 CF₃ CH₂OCH₂CH₂OMe CF₃ H 10-24CF₃ 10-25 Et Cl CF₃ H 10-26 Et Me CF₃ H 10-27 Et CH₂OMe CF₃ H 10-28 Et(1,1-dioxido-1,2- CF₃ H thiadiazolidin- 1-yl)methyl 10-29 EtCH₂OCH₂CH₂OMe CF₃ H 10-30 Et 10-31 n-Pr Cl CF₃ H 10-32 n-Pr Me CF₃ H10-33 n-Pr CH₂OMe CF₃ H 10-34 n-Pr (1,1-dioxido-1,2- CF₃ Hthiadiazolidin- 1-yl)methyl 10-35 n-Pr CH₂OCH₂CH₂OMe CF₃ H 10-36 n-Pr10-37 i-Pr Cl CF₃ H 10-38 i-Pr Me CF₃ H 10-39 i-Pr CH₂OMe CF₃ H 10-40i-Pr (1,1-dioxido-1,2- CF₃ H thiadiazolidin- 1-yl)methyl 10-41 i-PrCH₂OCH₂CH₂OMe CF₃ H 10-42 i-Pr 10-43 t-Bu Cl CF₃ H 10-44 t-Bu Me CF₃ H10-45 t-Bu CH₂OMe CF₃ H 10-46 t-Bu (1,1-dioxido-1,2- CF₃ Hthiadiazolidin- 1-yl)methyl 10-47 t-Bu CH₂OCH₂CH₂OMe CF₃ H 10-48 t-Bu10-49 (CH₂)₂CN Cl CF₃ H 11.27 (s, 1H), 8.88 (s, 1H), 8.49 (d, 1H), 8.14(d, 1H), 7.96 (d, 1H), 3.35 (s, 3H), 2.83-2.80 (m, 4H) 10-50 (CH₂)₂CN MeCF₃ H 10-51 (CH₂)₂CN CH₂OMe CF₃ H 10-52 (CH₂)₂CN (1,1-dioxido-1,2- CF₃ Hthiadiazolidin- 1-yl)methyl 10-53 (CH₂)₂CN CH₂OCH₂CH₂OMe CF₃ H

B. FORMULATION EXAMPLES

-   a) A dusting product is obtained by mixing 10 parts by weight of a    compound of the formula (I) and/or salts thereof and 90 parts by    weight of talc as an inert substance and comminuting the mixture in    a hammer mill.-   b) A readily water-dispersible wettable powder is obtained by mixing    25 parts by weight of a compound of the formula (I) and/or salts    thereof, 64 parts by weight of kaolin-containing quartz as an inert    substance, 10 parts by weight of potassium lignosulfonate and 1 part    by weight of sodium oleoylmethyltaurate as a wetting agent and    dispersant, and grinding the mixture in a pinned-disk mill.-   c) A readily water-dispersible dispersion concentrate is obtained by    mixing 20 parts by weight of a compound of the formula (I) and/or    salts thereof with 6 parts by weight of alkylphenol polyglycol ether    (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether    (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling    range for example about 255 to above 277° C.) and grinding the    mixture in a friction ball mill to a fineness of below 5 microns.-   d) An emulsifiable concentrate is obtained from 15 parts by weight    of a compound of the formula (I) and/or salts thereof, 75 parts by    weight of cyclohexanone as a solvent and 10 parts by weight of    ethoxylated nonylphenol as an emulsifier.-   e) Water-dispersible granules are obtained by mixing    -   75 parts by weight of a compound of the formula (I) and/or salts        thereof,    -   10 parts by weight of calcium lignosulfonate,    -   5 parts by weight of sodium laurylsulfate,    -   3 parts by weight of polyvinyl alcohol and    -   7 parts by weight of kaolin,    -   grinding the mixture in a pinned-disk mill, and granulating the        powder in a fluidized bed by spray application of water as a        granulating liquid.-   f) Water-dispersible granules are also obtained by homogenizing and    precomminuting, in a colloid mill,    -   25 parts by weight of a compound of the formula (I) and/or salts        thereof,    -   5 parts by weight of sodium        2,2′-dinaphthylmethane-6,6′-disulfonate,    -   2 parts by weight of sodium oleoylmethyltaurate,    -   1 part by weight of polyvinyl alcohol,    -   17 parts by weight of calcium carbonate and    -   50 parts by weight of water,    -   then grinding the mixture in a bead mill and atomizing and        drying the suspension thus obtained in a spray tower by means of        a one-phase nozzle.

C. BIOLOGICAL EXAMPLES 1. Pre-Emergence Herbicidal Action AgainstHarmful Plants

Seeds of monocotyledonous and dicotyledonous weed plants and crop plantsare laid out in wood-fiber pots in sandy loam and covered with soil. Thecompounds according to the invention, formulated in the form of wettablepowders (WP) or as emulsion concentrates (EC), are then applied to thesurface of the soil cover in the form of an aqueous suspension oremulsion at a water application rate equating to 600 to 800 I/ha, withaddition of 0.2% wetting agent. After the treatment, the pots are placedin a greenhouse and kept under good growth conditions for the testplants. The damage to the test plants is assessed visually after a testperiod of 3 weeks by comparison with untreated controls (herbicidalactivity in percent (%): 100% activity=the plants have died, 0%activity=like control plants). Here, for example, compounds No. 1-173,1-284, 1-293, 1-294, 1-295, 2-163, 2-173, 2-293, 2-295, 5-163 and 5-343,at an application rate of 320 g/ha, have an activity of at least 80%against

Abutilon theophrasti, Amaranthus retroflexus and Veronica persica.

2. Post-Emergence Herbicidal Action Against Harmful Plants

Seeds of monocotyledonous and dicotyledonous weed plants and crop plantsare laid out in wood fiber pots in sandy loam, covered with soil andcultivated in a greenhouse under good growth conditions. 2 to 3 weeksafter sowing, the test plants are treated at the one-leaf stage. Thecompounds according to the invention, formulated in the form of wettablepowders (WP) or as emulsion concentrates (EC), are then sprayed onto thegreen parts of the plants in the form of an aqueous suspension oremulsion at a water application rate equating to 600 to 800 I/ha, withaddition of 0.2% wetting agent. After the test plants have been left tostand in the greenhouse under optimal growth conditions for about 3weeks, the action of the preparations is assessed visually in comparisonto untreated controls (herbicidal action in percent (%): 100%activity=the plants have died, 0% activity=like control plants). Here,for example, compounds No. 1-173, 1-284, 1-294, 1-295, 2-163, 2-294,2-295, 5-172, 5-343 and 9-343, at an application rate of 80 g/ha, havean activity of at least 80% against Abutilon theophrasti.

1. An N-(isoxazol-3-yl)arylcarboxamide of formula (I) and/or a saltthereof

in which A represents N or CY, R represents hydrogen, (C₁-C₆)-alkyl,(C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy, (C₂-C₆)-alkenyl, (C₂-C₆)-alkenyloxy,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-alkynyloxy,(C₂-C₆)-haloalkynyl, cyano-(C₁-C₆)-alkyl, cyano, nitro, methylsulfenyl,methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino,methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl,ethoxycarbonylmethyl, benzoyl, methylcarbonyl, piperidinylcarbonyl,trifluoromethylcarbonyl, halogen, amino, aminocarbonyl,methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, orheteroaryl, heterocyclyl or phenyl, each of which is substituted by sradicals from the group consisting of methyl, ethyl, methoxy,trifluoromethyl and halogen, X represents nitro, halogen, cyano, formyl,thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, COOR¹, OCOOR¹, NR¹COOR¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂,C(O)NR¹OR¹, OR², OCOR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R²,NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹,(C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂,(C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², NR₁R₂, P(O)(OR⁵)₂,CH₂P(O)(OR⁵)₂, (C₁-C₆)-alkyl- heteroaryl, (C₁-C₆)-alkyl-heterocyclyl,where the two last-mentioned radicals are each substituted by s radicalsfrom the group consisting of halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy and halo-(C₁-C₆)-alkoxy, andwhere heterocyclyl carries n oxo groups, Y represents hydrogen, nitro,halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,halo-(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl,halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, COR¹, COOR¹, OCOOR¹, NR¹COOR¹,C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂, CO(NOR¹)R¹, CHNOR¹, CH₂ONCR³)₂,NR¹SO₂R², NR¹COR¹, OR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂(C₁-C₆)-alkyl-S(O)_(n)R², NS(O)R⁶R⁷, S(O)R⁸NR⁹, (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹,(C₁-C₆)-alkyl-CN, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²,N(R¹)₂, P(O)(OR⁵)₂, CH₂P(O)(OR⁵)₂, (C₁-C₆)-alkylphenyl,(C₁-C₆)-alkylheteroaryl, (C₁-C₆)-alkylheterocyclyl, phenyl, heteroarylor heterocyclyl, where the 6 last-mentioned radicals are eachsubstituted by s radicals from the group consisting of halogen, nitro,cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, and where heterocyclylcarries 0 to 2 oxo groups, Z represents halogen, cyano, thiocyanato,nitro, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,halo-(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, COOR¹, OCOOR¹, NR¹COOR¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂,C(O)NR¹OR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹,(C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹,(C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-SO₂OR¹,(C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹,(C₁-C₆)-alkyl-NR¹SO₂R², NR¹R², P(O)(OR⁵)₂, heteroaryl, heterocyclyl orphenyl, where the three last-mentioned radicals are each substituted bys radicals from the group consisting of halogen, nitro, cyano,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy or halo-(C₁-C₆)-alkoxy, and whereheterocyclyl carries 0 to 2 oxo groups, or Z may also represent hydrogenif Y represents the S(O)_(n)R² radical, V represents hydrogen,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy,S(O)_(n)—(C₁-C₆)-alkyl, S(O)_(n)—(C₁-C₆)-haloalkyl,(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, halogen, nitro or cyano, R¹ representshydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocycl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 last-mentioned radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR⁴,NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries 0to 2 oxo groups, R² represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl,(C₂-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl,(C₃-C₆)-halocycloalkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl,heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 last-mentioned radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR⁴,NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries 0to 2 oxo groups, R³ represents hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,R⁴ represents (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl or phenyl, R⁵represents methyl or ethyl, R⁶ and R⁷ independently of one another eachrepresent (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, phenyl,heteroaryl or heterocyclyl, where the three last-mentioned radicals areeach substituted by s radicals from the group consisting of nitro,halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R²(O)_(n)S,R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl, and where heterocyclylcarries n oxo groups, or R⁶ and R⁷ together with the sulfur atom towhich they are attached form a 3- to 8-membered unsaturated, partlysaturated or saturated ring which contains, apart from the carbon atomsand apart from the sulfur atom of the sulfoximino group, in each case mring members from the group consisting of N(R¹), O and S(O)_(n), andwhere this ring is in each case substituted by s radicals from the groupconsisting of nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, R¹O(O)C, (R¹)₂N(O)C, R¹O,(R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl, andwhere this ring carries n oxo groups, R⁸ represents (C₁-C₆)-alkyl,(C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, each of which is substituted by sradicals from the group consisting of nitro, halogen, cyano,thiocyanato, (C₃-C₆)-cycloalkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C,(R¹)₂N(O)C, R¹(R¹O)N(O)C, R²(O)₂S(R¹)N(O)C, R¹O(O)₂S(R¹)N(O)C,(R¹)₂N(O)₂S(R¹)N(O)C, R¹S(O)C, R¹O, R¹(O)CO, R²(O)₂SO, R²O(O)CO,(R¹)₂N(O)CO, (R¹)₂N, R¹O(R¹)N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N,(R¹)₂N(O)C(R¹)N, R¹O(O)₂S(R¹)N, (R¹)₂N(O)₂S(R¹)N, R²(O)S, R¹C(O)S,R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S, R²O(O)C(R¹)N(O)₂S,(R¹)₂N(O)C(R¹)N(O)₂S and (R⁵O)₂(P)P, or (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkenyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl,heteroaryl-(C₁-C₆)-alkyl, heterocyclyl, heterocyclyl-(C₁-C₆)-alkyl,phenyl-O—(C₁-C₆)-alkyl, heteroaryl-O—(C₁-C₆)-alkyl,heterocyclyl-O—(C₁-C₆)-alkyl, phenyl-N(R¹)—(C₁-C₆)-alkyl,heteroaryl-N(R¹)—(C₁-C₆)-alkyl, heterocyclyl-N(R¹)—(C₁-C₆)-alkyl,phenyl-S(O)_(n)—(C₁-C₆)-alkyl, heteroaryl-S(O)_(n)—(C₁-C₆)-alkyl orheterocyclyl-S(O)_(n)—(C₁-C₆)-alkyl, each of which is substituted in thecyclic moiety by s radicals from the group consisting of nitro, halogen,cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N(O)C,R¹(R¹O)N(O)C, R²(O)₂S(R¹)N(O)C, R¹O(O)₂S(R¹)N(O)C, (R¹)₂N(O)₂S(R¹)N(O)C,R¹S(O)C, R¹O, R¹(O)CO, R²(O)₂SO, R²O(O)CO, (R¹)₂N(O)CO, (R¹)₂N,R¹O(R¹)N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N,R¹O(O)₂S(R¹)N, (R¹)₂N(O)₂S(R¹)N, R²(O)_(n)S, R¹C(O)S, R¹O(O)₂S,(R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S, R²O(O)C(R¹)N(O)₂S, (R¹)₂N(O)C(R¹)N(O)₂S,(R⁵O)₂(O)P and R¹O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxogroups, R⁹ represents hydrogen, nitro, halogen, cyano, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₃-C₆)-alkenyl, halo-(C₃-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, R¹(O)C, R²O(O)C, (R¹)₂N(O)C,R²S(O)C, (R¹)₂N(S)C, R¹(R¹O)N(O)C, R²(O)₂S(R¹)N(O)C,(R¹)₂N(O)₂S(R¹)N(O)C, R¹O, (R¹)₂N, R²(O)_(n)S,(R²)₃Si—(C₁-C₆)-alkyl-(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S,R²O(O)C(R¹)N(O)₂S, (R¹)₂N(O)C(R¹)N(O)₂S, R²(O)₂S(R¹)N(O)₂S, (R⁵O)₂(O)P,(R²)₃Si, R¹(O)C—(C₁-C₆)-alkyl, R¹O(O)C—(C₁-C₆)-alkyl,(R¹)₂N(O)C—(C₁-C₆)-alkyl, (R¹O)(R¹)N(O)C—(C₁-C₆)-alkyl,R²(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, R¹O(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl,(R¹)₂N(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl,R¹(O)CO—(C₁-C₆)-alkyl, R²(O)₂SO—(C₁-C₆)-alkyl, R²O(O)CO—(C₁-C₆)-alkyl,(R¹)₂N(O)CO—(C₁-C₆)-alkyl, (R¹)₂N—(C₁-C₆)-alkyl,R¹(O)C(R¹)N—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N—(C₁-C₆)-alkyl,R²O(O)C(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N—(C₁-C₆)-alkyl,R¹O(O)₂S(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S(R¹)N—(C₁-C₆)-alkyl,R²(O)_(n)S—(C₁-C₆)-alkyl, R¹O(O)₂S—(C₁-C₆)-alkyl,(R¹)₂N(O)₂S—(C₁-C₆)-alkyl, R¹(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl,R²O(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl,(R⁵O)₂(O)P—(C₁-C₆)-alkyl, (R²)₃Si—(C₁-C₆)-alkyl, or phenyl, heteroaryl,heterocyclyl, phenyl-(C₁-C₆)-alkyl, heteroaryl-(C₁-C₆)-alkyl orheterocyclyl-(C₁-C₆)-alkyl, each of which is substituted in the cyclicmoiety by s radicals from the group consisting of nitro, halogen, cyano,thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S andR¹O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxo groups, mrepresents 0, 1, 2, 3 or 4, n represents 0, 1 or 2, s represents 0, 1, 2or 3, except for compounds in which R and Y each represent hydrogen andat the same time a) Z represents fluorine and X represents nitro,bromine or chlorine, or b) Z represents chlorine and X representschlorine, or c) Z represents methoxy and X represents methoxy, or d) Zrepresents ethoxy and X represents ethoxy, or e) Z represents methylsulfide and X represents methoxy.
 2. TheN-(isoxazol-3-yl)arylcarboxamide and/or salt as claimed in claim 1 inwhich A represents N or CY, X represents nitro, halogen, cyano,thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, COR¹, OR², OCOR¹, OSO₂R²,S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹,(C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹,(C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-SO₂OR¹,(C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹or (C₁-C₆)-alkyl-NR¹SO₂R², (C₁-C₆)-alkyl-heteroaryl,(C₁-C₆)-alkyl-heterocyclyl, where the two last-mentioned radicals eachby s radicals from the group consisting of halogen, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy andhalo-(C₁-C₆)-alkoxy, and where heterocyclyl carries 0 to 2 oxo groups, Yrepresents hydrogen, nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkenyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, OR¹, COOR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, N(R¹)₂,NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹,(C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂,(C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², (C₁-C₆)-alkylphenyl,(C₁-C₆)-alkyl-heteroaryl, (C₁-C₆)-alkyl-heterocyclyl, phenyl, heteroarylor heterocyclyl, where the 6 last-mentioned radicals are eachsubstituted by s radicals from the group consisting of halogen, nitro,cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, and where heterocyclylcarries 0 to 2 oxo groups, Z represents halogen, cyano, thiocyanato,nitro, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, COOR¹, C(O)N(R¹)₂, C(O)NR¹OR¹, OSO₂R², S(O)_(n)R², SO₂OR¹,SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R²,(C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R²,(C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²,1,2,4-triazol-1-yl, or Z may also represent hydrogen if Y represents theS(O)_(n)R² radical, V represents hydrogen, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy,S(O)_(n)—(C₁-C₆)-alkyl, S(O)_(n)—(C₁-C₆)-haloalkyl,(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, halogen, nitro or cyano, R representshydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, cyano-(C₁-C₆)-alkyl, cyano,methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino,methoxymethyl, or heteroaryl, heterocyclyl or phenyl, each of which issubstituted by s radicals from the group consisting of methyl, ethyl,methoxy, trifluoromethyl and halogen, R¹ represents hydrogen,(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl or(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 16 last-mentioned radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, NR³COR³, NR³SO₂R⁴,CO₂R³, CON(R³)₂ and (C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and whereheterocyclyl carries 0 to 2 oxo groups, R² represents (C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl or(C₁-C₆)-alkyl-NR³-heterocyclyl, where these radicals are substituted bys radicals from the group consisting of cyano, halogen, nitro, OR³,S(O)_(n)R⁴, N(R³)₂, NR³OR³, NR³SO₂R⁴, COR³, OCOR³, NR³COR³, CO₂R³,CON(R³)₂ and (C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and whereheterocyclyl carries 0 to 2 oxo groups, R³ represents hydrogen,(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl or(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, R⁴ represents (C₁-C₆)-alkyl,(C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, R⁶ and R⁷ independently of oneanother each represent (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, phenyl,heteroaryl or heterocyclyl, where the three last-mentioned radicals areeach substituted by s radicals from the group consisting of nitro,halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, R¹O(O)C, (R¹)₂N(O)C, R¹O,(R¹)₂N, R²(O)_(n)S and R¹O—(C₁-C₆)-alkyl, and where heterocyclyl carriesn oxo groups, or R⁶ and R⁷ together with the sulfur atom to which theyare attached form a 3- to 8-membered unsaturated, partly saturated orsaturated ring which contains, in addition to the carbon atoms and inaddition to the sulfur atom of the sulfoximino group, in each case mring members from the group consisting of N(R¹), O and S(O)_(n), andwhere this ring is in each case substituted by s radicals from the groupconsisting of halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, R¹O(O)C,(R¹)₂N(O)C, R¹O, (R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S andR¹O—(C₁-C₆)-alkyl, and where this ring carries n oxo groups, R⁸represents (C₁-C₆)-alkyl which is in each case substituted by s radicalsfrom the group consisting of halogen, cyano, (C₃-C₆)-cycloalkyl, R¹(O)C,R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N(O)C, R²(O)₂S(R¹)N(O)C, R¹O, (R¹)₂N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N, R²(O)_(n)S,R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S, R²O(O)C(R¹)N(O)₂S and(R¹)₂N(O)C(R¹)N(O)₂S or (C₃-C₆)-cycloalkyl which is in each casesubstituted by s radicals from the group consisting of halogen,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, R¹O(O)C and(R¹)₂N(O)C, R⁹ represents hydrogen, nitro, cyano, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,R¹(O)C, R²O(O)C, (R¹)₂N(O)C, R²(O)₂S, R¹(O)C—(C₁-C₆)-alkyl,R¹O(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)C—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl,(R¹)₂N—(C₁-C₆)-alkyl or R²(O)_(n)S—(C₁-C₆)-alkyl, m represents 0, 1 or2, n represents 0, 1 or 2, s represents 0, 1, 2 or 3, except forcompounds in which R and Y each represent hydrogen and at the same timea) Z represents fluorine and X represents nitro, bromine or chlorine, orb) Z represents chlorine and X represents chlorine, or c) Z representsmethoxy and X represents methoxy, or d) Z represents ethoxy and Xrepresents ethoxy, or e) Z represents methyl sulfide and X representsmethoxy.
 3. The N-(isoxazol-3-yl)arylcarboxamide and/or salt as claimedin claim 1 in which A represents N or CY, X represents nitro, halogen,cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, OR²,S(O)_(n)R², (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹,(C₁-C₆)-alkyl-NR¹SO₂R², (C₁-C₆)-alkylheteroaryl,(C₁-C₆)-alkylheterocyclyl, where the two last-mentioned radicals areeach substituted by s radicals from the group consisting of halogen,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, S(O)_(n)—(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, and where heterocyclyl carries 0 to2 oxo groups, Y hydrogen, nitro, halogen, cyano, (C₁-C₆)-alkyl,(C₁-C₆)-haloalkyl, OR¹, S(O)_(n)R², SO₂N(R¹)₂, N(R¹)₂, NR¹SO₂R²,NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹,(C₁-C₆)-alkyl-NR¹SO₂R², (C₁-C₆)-alkylphenyl, (C₁-C₆)-alkylheteroaryl,(C₁-C₆)-alkylheterocyclyl, phenyl, heteroaryl or heterocyclyl, where the6 last-mentioned radicals are each substituted by s radicals from thegroup consisting of halogen, nitro, cyano, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl andcyanomethyl, and where heterocyclyl carries 0 to 2 oxo groups, Zrepresents halogen, cyano, nitro, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, S(O)_(n)R², 1,2,4-triazol-1-yl,or Z may also represent hydrogen if Y represents the S(O)_(n)R² radical,V represents hydrogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, S(O)_(n)—(C₁-C₆)-alkyl,S(O)_(n)—(C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, halogen, nitroor cyano, R represents hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl,halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,cyano-(C₁-C₆)-alkyl, cyano, methylsulfenyl, methylsulfinyl,methylsulfonyl, acetylamino, halogen, amino, methoxymethyl, R¹represents hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl,(C₁-C₆)-alkylheteroaryl, heterocyclyl, (C₁-C₆)-alkylheterocyclyl,(C₁-C₆)-alkyl-O-heteroaryl, (C₁-C₆)-alkyl-O-heterocyclyl,(C₁-C₆)-alkyl-NR³-heteroaryl or (C₁-C₆)-alkyl-NR³-heterocyclyl, wherethe 16 last-mentioned radicals are substituted by s radicals from thegroup consisting of cyano, halogen, nitro, OR³, S(O)_(n)R⁴, N(R³)₂,NR³OR³, COR³, OCOR³, NR³COR³, NR³SO₂R⁴, CO₂R³, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries 0to 2 oxo groups, R² represents (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl or(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, where these three radicals mentionedabove are each substituted by s radicals from the group consisting ofhalogen and OR³, R³ represents hydrogen or (C₁-C₆)-alkyl, R⁴ represents(C₁-C₆)-alkyl, R⁶ and R⁷ independently of one another each representmethyl, ethyl or n-propyl, or R⁶ and R⁷ together with the sulfur atom towhich they are attached form a 5- or 6-membered saturated ring which, inaddition to the carbon atoms and in addition to the sulfur atom of thesulfoximino group, contains m oxygen atoms, R⁸ represents methyl, ethylor n-propyl, R⁹ represents hydrogen or cyano, m represents 0 or 1, nrepresents 0, 1 or 2, s represents 0, 1, 2 or 3, except for compounds inwhich R and Y each represent hydrogen and at the same time a) Zrepresents fluorine and X represents nitro, bromine or chlorine, or b) Zrepresents chlorine and X represents chlorine, or c) Z representsmethoxy and X represents methoxy, or d) Z represents ethoxy and Xrepresents ethoxy, or e) Z represents methyl sulfide and X representsmethoxy.
 4. A herbicidal composition characterized by a herbicidallyactive content of at least one compound of formula (I) as claimed inclaim
 1. 5. The herbicidal composition as claimed in claim 4 in amixture with one or more formulation auxiliaries.
 6. The herbicidalcomposition as claimed in claim 4, comprising at least one furtherpesticidally active substance from the group consisting of insecticides,acaricides, herbicides, fungicides, safeners, and growth regulators. 7.The herbicidal composition as claimed in claim 6, comprising a safener.8. The herbicidal composition as claimed in claim 7, comprisingcyprosulfamide, cloquintocet-mexyl, mefenpyr-diethyl orisoxadifen-ethyl.
 9. The herbicidal composition as claimed in claim 6,comprising a further herbicide.
 10. A method for controlling unwantedplants, comprising applying an effective amount of at least one compoundof formula (I) as claimed in claim 1 to the plants and/or to a site ofthe unwanted plants.
 11. A compound of the formula (I) and/or salt asclaimed in claim 1 for controlling unwanted plants.
 12. A compoundand/or salt as claimed in claim 11, wherein the compounds of the formula(I) are capable of being used for controlling one or more unwantedplants in crops of useful plants.
 13. A compound and/or salt as claimedin claim 12, wherein the useful plants are transgenic useful plants. 14.4-(Trifluoromethyl)-1,2-oxazole-2-amine.
 15. 4(trifluoromethyl)-1,2-oxazole-3-amine capable of being used forpreparing a compound and/or salt as claimed in claim 1 where Rrepresents trifluoromethyl.
 16. A method for preparing a compound offormula (I) and/or salt of claim 1, wherein R represents trifluoromethylcomprising using 4-(trifluoromethyl)-1,2-oxazole-3-amine.